DOCSLIB.ORG

VITAMIN K1 | C31H46O2 - Pubchem

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
VITAMIN K1 | C31H46O2 - Pubchem VITAMIN K1 | C31H46O2 - PubChem https://pubchem.ncbi.nlm.nih.gov/compound/Phylloquinone#secti... NIH U.S. National Library of Medicine National Center for Biotechnology Information OPEN CHEMISTRY Search Compounds ! DATABASE VITAMIN K1 " Cite this Record # $ % & ' ( STRUCTURE VENDORS DRUG INFO PHARMACOLOGY LITERATURE PATENTS BIOACTIVITIES PubChem CID: 5284607 VITAMIN K1; Phytonadione; Phylloquinone; 84-80-0; Phytylmenadione; Chemical Names: Phyllochinon More... Molecular Formula: C31H46O2 Molecular Weight: 450.707 g/mol InChI Key: MBWXNTAXLNYFJB-NKFFZRIASA-N Drug Indication Therapeutic Uses Clinical Trials FDA Orange Book Drug Information: FDA UNII Safety Summary: Laboratory Chemical Safety Summary (LCSS) VITAMIN K1 is a family of phylloquinones that contains a ring of 2-methyl-1,4-naphthoquinone and an isoprenoid side chain. Members of this group of vitamin K 1 have only one double bond on the proximal isoprene unit. Rich sources of vitamin K 1 include green plants, algae, and photosynthetic bacteria. Vitamin K1 has antihemorrhagic and prothrombogenic activity. " from MeSH Vitamin K is a family of fat-soluble compounds with a common chemical structure based on 2-methyl-1, 4-naphthoquinone " Metabolite Description from Human Metabolome Database (HMDB) PUBCHEM ) COMPOUND ) VITAMIN K1 Modify Date: 2018-01-06; Create Date: 2004-09-16 1 di 57 12/01/18, 11:36 VITAMIN K1 | C31H46O2 - PubChem https://pubchem.ncbi.nlm.nih.gov/compound/Phylloquinone#secti... * Contents 1 2D Structure 2 3D Conformer 3 Names and Identifiers + 4 Chemical and Physical Properties 5 Related Records 6 Chemical Vendors 7 Drug and Medication Information 8 Pharmacology and Biochemistry 9 Use and Manufacturing 10 Identification 11 Safety and Hazards 12 Toxicity 13 Literature 14 Patents 15 Biomolecular Interactions and Pathways 16 Biological Test Results 17 Classification 18 Information Sources 2 di 57 12/01/18, 11:36 VITAMIN K1 | C31H46O2 - PubChem https://pubchem.ncbi.nlm.nih.gov/compound/Phylloquinone#secti... 1 2D Structure ! Search - Download . Get Image , Magnify " from PubChem 3 di 57 12/01/18, 11:36 VITAMIN K1 | C31H46O2 - PubChem https://pubchem.ncbi.nlm.nih.gov/compound/Phylloquinone#secti... 2 3D Conformer ! Search - Download . Get Image , Magnify / Show Hydrogens / Show Atoms 0 Animate " from PubChem 4 di 57 12/01/18, 11:36 VITAMIN K1 | C31H46O2 - PubChem https://pubchem.ncbi.nlm.nih.gov/compound/Phylloquinone#secti... 3 Names and Identifiers 3.1 Computed Descriptors 3.1.1 IUPAC Name 2-methyl-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione " from PubChem 3.1.2 InChI InChI=1S/C31H46O2 /c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(2 7)33/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+/t23-,24-/m1/s1 " from PubChem 3.1.3 InChI Key MBWXNTAXLNYFJB-NKFFZRIASA-N " from PubChem 3.1.4 Canonical SMILES CC1=C(C(=O)C2=CC=CC=C2C1=O)CC=C(C)CCCC(C)CCCC(C)CCCC(C)C " from PubChem 3.1.5 Isomeric SMILES CC1=C(C(=O)C2=CC=CC=C2C1=O)C/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C " from PubChem 3.2 Molecular Formula C31H46O2 " from PubChem 3.3 Other Identifiers 3.3.1 CAS 84-80-0 5 di 57 12/01/18, 11:36 VITAMIN K1 | C31H46O2 - PubChem https://pubchem.ncbi.nlm.nih.gov/compound/Phylloquinone#secti... " from ChemIDplus, DTP/NCI, DrugBank, EPA DSStox, European Chemicals Agency - ECHA, H… 11104-38-4 " from ChemIDplus, European Chemicals Agency - ECHA 79083-00-4 " from ChemIDplus, European Chemicals Agency - ECHA 12001-79-5 " from European Chemicals Agency - ECHA 81382-12-9 " from Human Metabolome Database (HMDB) 3.3.2 EC NumBer 201-564-2 " from European Chemicals Agency - ECHA 234-330-3 " from European Chemicals Agency - ECHA 234-408-7 " from European Chemicals Agency - ECHA 279-052-3 " from European Chemicals Agency - ECHA 3.3.3 NSC NumBer 760373 " from DTP/NCI 3.3.4 UNII S5Z3U87QHF " from DrugBank, FDA/SPL Indexing Data 3.3.5 Wikipedia Title (E)-phytonadione Description chemical compound " from Wikipedia 6 di 57 12/01/18, 11:36 VITAMIN K1 | C31H46O2 - PubChem https://pubchem.ncbi.nlm.nih.gov/compound/Phylloquinone#secti... 3.4 Synonyms 3.4.1 MeSH Entry Terms 1. Aquamephyton 2. Konakion 3. Phyllohydroquinone 4. Phylloquinone 5. Phytomenadione 6. Phytonadione 7. Vitamin K 1 8. Vitamin K1 " from MeSH 3.4.2 Depositor-Supplied Synonyms 1. VITAMIN K1 11. Kinadion 21. Kativ N 31. 2. phytonadione 12. Konakion 22. trans-Phylloquinone 32. 3. Phylloquinone 13. Mephyton 23. VitaminK1 33. 4. 84-80-0 14. Monodion 24. K-Ject 34. 5. Phytylmenadione 15. Kephton 25. UNII-S5Z3U87QHF 35. 6. Phyllochinon 16. Antihemorrhagic vitamin 26. Aquamephyton 36. 7. Phytomenadione 17. Synthex P 27. Fitomenadiona 37. 8. alpha-Phylloquinone 18. VITAMIN K 28. Phyllochinonum 38. 9. 3-Phytylmenadione 19. Mono-Kay 29. Phytomenadionum 39. 10. 2-Methyl-3-phytyl-1,4-naphthoquinone 20. Combinal K1 30. Phytonadionum 40. " from PubChem 7 di 57 12/01/18, 11:36 VITAMIN K1 | C31H46O2 - PubChem https://pubchem.ncbi.nlm.nih.gov/compound/Phylloquinone#secti... 4 Chemical and Physical Properties 4.1 Computed Properties Property Name Property Value Molecular Weight 450.707 g/mol Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2 Rotatable Bond Count 14 Complexity 696 AAADcfB4MAAAAAAAAAAAAAAAAAAAAAAAAAA wQAAAAAAAAACBAAAAGgAAAAAADQSAmAAyAI CACTVS Substructure Key Fingerprint AAAACIAqBSAAACAAAkAAAIiAEAAMgIIDKAFRCA IQAggAAIiYcJiMCOgAAAAAAQAAAAAAAAACAAA AAAAAAAAA== Topological Polar Surface Area 34.1 A^2 Monoisotopic Mass 450.35 g/mol Exact Mass 450.35 g/mol XLogP3-AA 10.9 Compound Is Canonicalized true Formal Charge 0 Heavy Atom Count 33 Defined Atom Stereocenter Count 2 Undefined Atom Stereocenter Count 0 Defined Bond Stereocenter Count 1 Undefined Bond Stereocenter Count 0 Isotope Atom Count 0 Covalently-Bonded Unit Count 1 " from PubChem 4.2 Experimental Properties 4.2.1 Physical Description Solid " from Human Metabolome Database (HMDB) 8 di 57 12/01/18, 11:36 VITAMIN K1 | C31H46O2 - PubChem https://pubchem.ncbi.nlm.nih.gov/compound/Phylloquinone#secti... Liquid " from Human Metabolome Database (HMDB) 4.2.2 Color Yellow viscous oil O'Neil, M.J. (ed.). The MerCk Index - An EnCyClopedia of ChemiCals, Drugs, and BiologiCals. 13th Edition, Whitehouse Station, NJ: MerCk and Co., InC., 2001., p. 1532 " from HSDB LIGHT-YELLOW SOLIDS OR OILS Osol, A. and J.E. Hoover, et al. (eds.). Remington's PharmaCeutiCal SCienCes. 15th ed. Easton, Pennsylvania: MaCk Publishing Co., 1975., p. 942 " from HSDB Pale yellow oil or yellow crystals Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 10th ed. Volumes 1-3 New York, NY: John Wiley & Sons InC., 1999., p. V2 3690 " from HSDB Clear, yellow to amber, viscous, odourless liquid IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International AgenCy for ResearCh on CanCer, 1972-PRESENT. (Multivolume work). Available at: http://monographs.iarC.fr/ENG/Classification/index.php , p. V76 422 (2000) " from HSDB 4.2.3 Odor Odorless Lewis, R.J., Sr (Ed.). Hawley's Condensed ChemiCal DiCtionary. 13th ed. New York, NY: John Wiley & Sons, InC. 1997., p. 880 " from HSDB 4.2.4 Boiling Point 142.5 °C at 1.00E-03 mm Hg PhysProp " from DrugBank 140-145 deg C @ 0.001 mm Hg Lide, DR (ed.). CRC Handbook of Chemistry and PhysiCs. 81st Edition. CRC Press LLC, BoCa Raton: FL 2000, p. 3-216 " from HSDB 4.2.5 Melting Point 9 di 57 12/01/18, 11:36 VITAMIN K1 | C31H46O2 - PubChem https://pubchem.ncbi.nlm.nih.gov/compound/Phylloquinone#secti... -20 °C PhysProp " from DrugBank -20 deg C Lide, DR (ed.). CRC Handbook of Chemistry and PhysiCs. 81st Edition. CRC Press LLC, BoCa Raton: FL 2000, p. 3-216 " from HSDB -20 °C " from Human Metabolome Database (HMDB) 4.2.6 Solubility Water Solubility Insoluble in water " from DrugBank Insoluble in water; sparingly soluble in methanol; sol in ethanol; sol in acetone, benzene, petroleum ether, hexane, and dioxane; sol in chloroform, and other fat solvents; sol in vegetable oils O'Neil, M.J. (ed.). The MerCk Index - An EnCyClopedia of ChemiCals, Drugs, and BiologiCals. 13th Edition, Whitehouse Station, NJ: MerCk and Co., InC., 2001., p. 1322 " from HSDB SOL IN FATS Goodman, L.S., and A. Gilman. (eds.) The PharmaCologiCal Basis of TherapeutiCs. 5th ed. New York: MaCmillan Publishing Co., InC., 1975., p. 1592 " from HSDB 5.92e-05 g/L " from Human Metabolome Database (HMDB) 4.2.7 Density 0.964 @ 25 deg C/25 deg C O'Neil, M.J. (ed.). The MerCk Index - An EnCyClopedia of ChemiCals, Drugs, and BiologiCals. 13th Edition, Whitehouse Station, NJ: MerCk and Co., InC., 2001., p. 1322 " from HSDB 4.2.8 LogP 9.3 " from DrugBank, Human Metabolome Database (HMDB) 4.2.9 Stability 10 di 57 12/01/18, 11:36 VITAMIN K1 | C31H46O2 - PubChem https://pubchem.ncbi.nlm.nih.gov/compound/Phylloquinone#secti... STABLE TO AIR & MOISTURE, BUT DECOMP IN SUNLIGHT The MerCk Index. 9th ed. Rahway, New Jersey: MerCk & Co., InC., 1976., p. 1291 " from HSDB STABLE IN QUINONE FORM Osol, A. and J.E. Hoover, et al. (eds.). Remington's PharmaCeutiCal SCienCes. 15th ed. Easton, Pennsylvania: MaCk Publishing Co., 1975., p. 943 " from HSDB UNAFFECTED BY DIL ACIDS, DESTROYED BY ALKALI HYDROXIDES & REDUCING AGENTS The MerCk Index. 9th ed. Rahway, New Jersey: MerCk & Co., InC., 1976., p. 1291 " from HSDB Phytonadione is stable to heat and moisture and may be autoclaved. MCEvoy, G.K. (ed.). AmeriCan Hospital Formulary ServiCe- Drug Information 2002. Bethesda, MD: AmeriCan SoCiety of Health-System PharmaCists, Inc. 2002 (Plus Supplements)., p. 3566 " from HSDB 4.2.10 Decomposition When heated to decomposition it emits acrid smoke and irritating fumes.
Load more

Recommended publications
  • Retention Indices for Frequently Reported Compounds of Plant Essential Oils
    Retention Indices for Frequently Reported Compounds of Plant Essential Oils V. I. Babushok,a) P. J. Linstrom, and I. G. Zenkevichb) National Institute of Standards and Technology, Gaithersburg, Maryland 20899, USA (Received 1 August 2011; accepted 27 September 2011; published online 29 November 2011) Gas chromatographic retention indices were evaluated for 505 frequently reported plant essential oil components using a large retention index database. Retention data are presented for three types of commonly used stationary phases: dimethyl silicone (nonpolar), dimethyl sili- cone with 5% phenyl groups (slightly polar), and polyethylene glycol (polar) stationary phases. The evaluations are based on the treatment of multiple measurements with the number of data records ranging from about 5 to 800 per compound. Data analysis was limited to temperature programmed conditions. The data reported include the average and median values of retention index with standard deviations and confidence intervals. VC 2011 by the U.S. Secretary of Commerce on behalf of the United States. All rights reserved. [doi:10.1063/1.3653552] Key words: essential oils; gas chromatography; Kova´ts indices; linear indices; retention indices; identification; flavor; olfaction. CONTENTS 1. Introduction The practical applications of plant essential oils are very 1. Introduction................................ 1 diverse. They are used for the production of food, drugs, per- fumes, aromatherapy, and many other applications.1–4 The 2. Retention Indices ........................... 2 need for identification of essential oil components ranges 3. Retention Data Presentation and Discussion . 2 from product quality control to basic research. The identifi- 4. Summary.................................. 45 cation of unknown compounds remains a complex problem, in spite of great progress made in analytical techniques over 5.
    [Show full text]
  • Vitamin E: Food Chemistry, Composition, and Analysis, Ronald Eitenmiller and Junsoo Lee
    Vitamin E Copyright © 2004 by Marcel Dekker, Inc. FOOD SCIENCE AND TECHNOLOGY A Series of Monographs, Textbooks, and Reference Books EDITORIAL BOARD Senior Editors Owen R.Fennema University of Wisconsin-Madison Y.H.Hui Science Technology System Marcus Karel Rutgers University (emeritus) Pieter Walstra Wageningen University John R.Whitaker University of California-Davis Additives P.Michael Davidson University of Tennessee-Knoxville Dairy science James L.Steele University of Wisconsin-Madison Flavor chemistry and sensory analysis John H.Thorngate III University of California-Davis Food engineering Daryl B.Lund University of Wisconsin-Madison Food lipids and flavors David B.Min Ohio State University Food proteins/food chemistry Rickey Y.Yada University of Guelph Health and disease Seppo Salminen University of Turku, Finland Nutrition and nutraceuticals Mark Dreher Mead Johnson Nutritionals Phase transition/food microstructure Richard W.Hartel University of Wisconsin-Madison Processing and preservation Gustavo V.Barbosa-Cánovas Washington State University-Pullman Safety and toxicology Sanford Miller University of Texas-Austin 1. Flavor Research: Principles and Techniques, R.Teranishi, I.Hornstein, P.Issenberg, and E.L.Wick 2. Principles of Enzymology for the Food Sciences, John R.Whitaker 3. Low-Temperature Preservation of Foods and Living Matter, Owen R. Fennema, William D.Powrie, and Elmer H.Marth 4. Principles of Food Science Part I: Food Chemistry, edited by Owen R.Fennema Part II: Physical Principles of Food Preservation, Marcus Karel, Owen R.Fennema, and Daryl B.Lund 5. Food Emulsions, edited by Stig E.Friberg 6. Nutritional and Safety Aspects of Food Processing, edited by Steven R.Tannenbaum 7. Flavor Research: Recent Advances, edited by R.Teranishi, Robert A.
    [Show full text]
  • GRAS Notice (GRN) No. 761, Esterified Propoxylated Glycerol
    GRAS Notice (GRN) No. 761 https://www.fda.gov/food/generally-recognized-safe-gras/gras-notice-inventory February 20, 2018 Office ofFood Additive Safety HFS-200 Center for foodSafetyand Applied Nutrition food and Drug Administratioo 5001 Campus Drive College Park, MD, 20740 Dear Sir or Madam: Accompanying this letterisa notice pursuantto regulationsofthe Food and Orug Administration found at 21 CFR Part 170 settingforth the basis forthe conclusion reached by the submitter, Choco Finesse, LLC, that esterified propoxylated glycerol (EPG) is generally recognized as safe underthe intended conditions ofuse described in the notice. The notice is contained in a binder. In addition, we include a CD that contains a complete copyofthe notice. I hereby certify thatthe electronicfilescontained onthe flash drivewere scanned forviruses priorto submission, and thuscertified as beingvirus-free using Symantec Endpoint Protection. Sine I,/ .. (b) (6) '---'--------..... David Rowe President Phone: 317-694-3601 Email: drowe@chocofi nesse .com Ft -1 2 2 2018 z., ,..,.. ,. ; FOOD ADDITivE SAFETY GRAS NOTICE FOR ESTERIFIED PROPOXYLATED GLVCEROL {EPG) FOR USE IN SELECT COMMERCIAL FRYING APPLICATIONS Prepared for: Office of Food Additive Safety (HFS-200} Center for Food Safety and Applied Nutrition Food and Drug Administration 5001 Campus Drive College Park, MD 20740 Prepared by: Choco Finesse, LLC 5019 N. Meridian Street Indianapolis, Indiana 46208 February 20, 2018 rR1~~~~~~[Q) FEB 2 2 2018 OFFICE OF FOOD ADDmVE SAFETY GRAS Notice for Esterified Propoxylated Glycerol (EPG) for Use in Select Commercial Frying Applications TABLE OF CONTENTS Part 1. §170.225 Signed Statements and Certification ..................................................................................... 4 1.1 Name and Address of Notifier .................................................................................................. 4 1.2 Common Name of Notified Substance ....................................................................................
    [Show full text]
  • Chemistry of the Main Component of Essential Oil of Litsea Cubeba and Its Derivatives
    Open Journal of Forestry, 2014, 4, 457-466 Published Online October 2014 in SciRes. http://www.scirp.org/journal/ojf http://dx.doi.org/10.4236/ojf.2014.45050 Chemistry of the Main Component of Essential Oil of Litsea cubeba and Its Derivatives Lisong Hu, Menghao Du, Jingping Zhang, Yangdong Wang Research Institute of Subtropical Forestry Chinese Academy of Forestry, Fuyang, China Email: [email protected] Received 8 July 2014; revised 11 August 2014; accepted 26 August 2014 Copyright © 2014 by authors and Scientific Research Publishing Inc. This work is licensed under the Creative Commons Attribution International License (CC BY). http://creativecommons.org/licenses/by/4.0/ Abstract The tree of Litsea cubeba is widely spread in China, Indonesia and other part of Southeast Asia. The essential oil of Litsea cubeba (EOLC) is obtained by steam distillation from the pepper-like fruits tree Litsea cubeba. The EOLC consists of about 29 active compounds. Among them, citral is the main component; the content of citral is nearly 80% of the EOLC. Due to the special function group, citral is easy to react with many chemicals. Thus, EOLC is usually applied as starting ma- terial to carry out aldol condensation, reduction, and six-member ring forming reaction. The EOLC is extensively employed to synthesis of geranal nitriles, pseudonoe, ionone, methyl ionone, Vita- min E and Vitamin A. These products are broadly applied in the fields of fragrance, perfume, med- icine and so on. This paper presents comprehensive utilization of EOLC as raw materials to syn- thesize many active chemicals. Keywords Litsea cubeba, Essential Oil, Citral, Synthesis 1.
    [Show full text]
  • Peroxisomal Trans-2-Enoyl-Coa Reductase Is Involved in Phytol Degradation
    View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Elsevier - Publisher Connector FEBS Letters 580 (2006) 2092–2096 Peroxisomal trans-2-enoyl-CoA reductase is involved in phytol degradation J. Gloerich, J.P.N. Ruiter, D.M. van den Brink, R. Ofman, S. Ferdinandusse, R.J.A. Wanders* Laboratory Genetic Metabolic Diseases (F0-224), Departments of Clinical Chemistry and Pediatrics, Emma’s Children’s Hospital, Academic Medical Center, University of Amsterdam, Meibergdreef 9, 1105 AZ Amsterdam, The Netherlands Received 15 February 2006; accepted 4 March 2006 Available online 10 March 2006 Edited by Sandro Sonnino the peroxisomal acyl-CoA oxidases anymore. For further Abstract Phytol is a naturally occurring precursor of phytanic acid. The last step in the conversion of phytol to phytanoyl-CoA breakdown, the chain-shortened product is transported to is the reduction of phytenoyl-CoA mediated by an, as yet, the mitochondrion [3], where it is totally degraded to acetyl- unidentified enzyme. A candidate for this reaction is a previously CoA and propionyl-CoA units [4]. Besides breakdown of described peroxisomal trans-2-enoyl-CoA reductase (TER). To pristanic acid, peroxisomal b-oxidation is also involved in investigate this, human TER was expressed in E. coli as an the degradation of very long-chain fatty acids, long-chain MBP-fusion protein. The purified recombinant protein was dicarboxylic acids and bile acid intermediates [4]. shown to have high reductase activity towards trans-phytenoyl- Another metabolic process that recently has been shown to CoA, but not towards the peroxisomal b-oxidation intermediates occur, at least partly, in the peroxisome is the degradation of C24:1-CoA and pristenoyl-CoA.
    [Show full text]
  • Anne Marie Api, Ph.D
    Anne Marie Api, Ph.D. W: +1-201-689-8089 ext. 103 C: +1-914-433-1205 Summary of Experience Research Institute for Fragrance Materials Inc. (RIFM) 1984-present Woodcliff Lake, New Jersey USA Vice President, Human Health Sciences 2006-present RIFM, the most comprehensive source worldwide for toxicology data, literature and information on the evaluation of fragrance materials is the international scientific authority for the safe use of fragrance materials. Combining an advanced knowledge of fragrance ingredient safety, senior leadership experience, an excellent work ethic and exceptional communication skills, I have established a quality record of managing fragrance ingredient safety at RIFM. I am committed to investigating new scientific methodologies to keep RIFM at the cutting edge of advancements in toxicology. I am also committed to education and inspiring others on current and future goals. Responsible for the human health scientific program. Continue to maintain and oversee implementation of the RIFM Safety Assessment program with respect to all human health endpoints as well as computational toxicology. Investigate and initiate new research and testing projects, including those that would involve development of new testing methodologies. I continue to promote and initiate new research projects that evaluate and improve test methodologies and assessment procedures to address the emerging safety challenges. Initiated and oversee the publication of the RIFM safety assessments on the Food and Chemical Toxicology Fragrance Material Safety Assessment Center (http://fragrancematerialsafetyresource.elsevier.com). This is a partnership between RIFM and Elsevier for an open access resource center. Initiated and continue to update an aggregate exposure model for providing a realistic exposure assessment to fragrance ingredients.
    [Show full text]
  • Tetrahydrogeranylgeraniol, a Precursor of Phytol in The
    Tetrahydrogeranylgeraniol, a Precursor of Phytol in the Biosynthesis of Chlorophyll a — Localization of the Double Bonds Siegrid Schoch and Wolfram Schäfer Botanisches Institut der Universität München, München und Max-Planck-Institut für Biochemie, Martinsried Z. Naturforsch. 33 c, 408—412 (1978) ; received March 23, 1978 Dedicated to Prof. Dr. A. Butenandt on the Occasion of His 75. Birthday Avena sativa, Gramineae, Oats, Chlorophyll Biosynthesis, Phytol Pheophytins esterified with phytol and tetrahydrogeranylgeraniol are isolated from etiolated oat seedlings after short (1 min) exposure to light and a subsequent dark period of 15 to 20 min. After saponification of the pheophytins, a mixture of the alcohols was isolated. The structure of tetra­ hydrogeranylgeraniol was established as 3,7,11,15-tetramethyl-zl2’14 hexadecadiene-l-ol (3a). The implications for chlorophyll biosynthesis are discussed. Introduction The number of double bonds in the alcohols have been established from the molecular ions in their During our research on the last steps of chloro­ mass spectra [3, 4]. The heaviest alcohol is P (4), phyll biosynthesis, we could isolate pheophytins the alcohols THGG (3), DHGG (2) and GG (1) which are esterified with not only phytol (P), but are smaller by 2, 4 and 6 mass units respectively. also with tetrahydrogeranylgeraniol (THGG), dihy- To further evaluate this sequence it is necessary drogeranylgeraniol (DHGG) and geranylgeraniol to establish the order of hydrogenation of the three (GG) [1]. double bonds zl-6, A-10, A-\4> when transforming Based on these findings, a biosynthetic sequence GG to P. has been proposed, in which chlorophyllide a is first As the pigments were available only in small esterified to Chl^G • This pigment should then hy­ amounts (5 — 10nmol/g fresh weight), the alcohols drogenated successively to CMdiigg > CIiIthgg and were identified and the double bonds localized by finally to Chip [1], The activated alcohol substrate gc-ms technique combined with microchemical proce­ for the esterification is probably geranylgeraniol- dures.
    [Show full text]
  • US5236950.Pdf
    |||||||||||||||| USOO.5236950A United States Patent (19) 11 Patent Number: 5,236,950 Aoyama et al. 45 Date of Patent: Aug. 17, 1993 (54) PROCESS FOR HAIR GROWTH 2652256 6/1977 Fed. Rep. of Germany . 2812978 10/1979 Fed. Rep. of Germany . 75) Inventors: Hajime Aoyama; Satoshi Ono; Osamu 3738405 5/1989 Fed. Rep. of Germany . Oohashi; Hirokazu Narita; Shuntaro 119.0002 10/1959 France, Takano, all of Toyama, Japan 60-004113 10/1985 Japan. 61-207321 9/1986 Japan . 73) Assignee: Toyama Chemical Co., Ltd., Tokyo, 8302390 7/1983 PCT Int'l Appl. Japan 780801 8/1957 United Kingdom . 923400 4/1963 United Kingdom . 21 Appl. No.: 311,945 944834 12/1963 United Kingdom. (22 Filed: Feb. 17, 1989 83/02390 7/1983 World int. Prop. O. (30) Foreign Application Priority Data OTHER PUBLICATIONS Feb. 18, 1988 JP Japan .................................. 63-33968 Derwent Abstract WPI Acc No. 75-62757W/38 Jun. 3, 1988 JP Japan ................................ 63.36824 (Takasago). 51) Int. Cl................................................. A61K 7/06 Derwent Abstract WPI Acc No. JP49069845 52 U.S. Cl. .................................... 514/478; 514/354; (Takasago). 514/356; 514/532; 514/556; 514/715; 514/738; Derwent-Ref: 60454Y/34 Nov. 1, 1976. 514/739 Derwent-Ref: 85-077293/13 Jul. 25, 1983. 58) Field of Search ................. 514/70,478, 556, 354, Derwent-Ref: 85-077294/13 Jul. 28, 1983. 514/356, 532, 715, 738 Derwent-Ref: 86-141951/22 Sep. 27, 1984. Derwent-Ref: 62505B/34 Dec. 27, 1977. (56) References Cited Chemical Abstracts, vol. 83, p. 435, 1975, No. 65330r, U.S. PATENT DOCUMENTS Yoshigi Hideki, et al., "Cosmetics With Improved 4,139,619 2/1979 Chidsey, III et al.
    [Show full text]
  • Open Natural Products Research: Curation and Dissemination of Biological Occurrences of Chemical Structures Through Wikidata
    bioRxiv preprint doi: https://doi.org/10.1101/2021.02.28.433265; this version posted March 1, 2021. The copyright holder has placed this preprint (which was not certified by peer review) in the Public Domain. It is no longer restricted by copyright. Anyone can legally share, reuse, remix, or adapt this material for any purpose without crediting the original authors. Open Natural Products Research: Curation and Dissemination of Biological Occurrences of Chemical Structures through Wikidata Adriano Rutz1,2, Maria Sorokina3, Jakub Galgonek4, Daniel Mietchen5, Egon Willighagen6, James Graham7, Ralf Stephan8, Roderic Page9, Jiˇr´ıVondr´aˇsek4, Christoph Steinbeck3, Guido F. Pauli7, Jean-Luc Wolfender1,2, Jonathan Bisson7, and Pierre-Marie Allard1,2 1School of Pharmaceutical Sciences, University of Geneva, CMU - Rue Michel-Servet 1, CH-1211 Geneva 4, Switzerland 2Institute of Pharmaceutical Sciences of Western Switzerland, University of Geneva, CMU - Rue Michel-Servet 1, CH-1211 Geneva 4, Switzerland 3Institute for Inorganic and Analytical Chemistry, Friedrich-Schiller-University Jena, Lessingstr. 8, 07732 Jena, Germany 4Institute of Organic Chemistry and Biochemistry of the CAS, Flemingovo n´amˇest´ı2, 166 10, Prague 6, Czech Republic 5School of Data Science, University of Virginia, Dell 1 Building, Charlottesville, Virginia 22904, United States 6Dept of Bioinformatics-BiGCaT, NUTRIM, Maastricht University, Universiteitssingel 50, NL-6229 ER, Maastricht, The Netherlands 7Center for Natural Product Technologies, Program for Collaborative Research
    [Show full text]
  • Acetylene in Organic Synthesis: Recent Progress and New Uses
    Review Acetylene in Organic Synthesis: Recent Progress and New Uses Vladimir V. Voronin 1, Maria S. Ledovskaya 1, Alexander S. Bogachenkov 1, Konstantin S. Rodygin 1 and Valentine P. Ananikov 1,2,* 1 Institute of Chemistry, Saint Petersburg State University, Universitetsky prospect 26, Peterhof 198504, Russia; [email protected] (V.V.V.); [email protected] (M.S.L.); [email protected] (A.S.B.); [email protected] (K.S.R.) 2 N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky prospect 47, Moscow 119991, Russia * Correspondence: [email protected] Received: 16 August 2018; Accepted: 17 September 2018; Published: 24 September 2018 Abstract: Recent progress in the leading synthetic applications of acetylene is discussed from the prospect of rapid development and novel opportunities. A diversity of reactions involving the acetylene molecule to carry out vinylation processes, cross-coupling reactions, synthesis of substituted alkynes, preparation of heterocycles and the construction of a number of functionalized molecules with different levels of molecular complexity were recently studied. Of particular importance is the utilization of acetylene in the synthesis of pharmaceutical substances and drugs. The increasing interest in acetylene and its involvement in organic transformations highlights a fascinating renaissance of this simplest alkyne molecule. Keywords: acetylene; vinylation; cross-coupling; addition reactions; drugs; pharmaceutical substances; biologically active molecule; monomers; polymers 1. Introduction Since the discovery of acetylene, new areas of acetylene chemistry have been continuously developed. The rich scope of chemical transformations available for a C≡C triple bond can be exemplified by coupling [1–5] and addition reactions [6,7].
    [Show full text]
  • Process for Producing 6-Methyl-2-Heptanone Analogues, and Process for Producing Phyton and Isophytol
    Europäisches Patentamt *EP000816321B1* (19) European Patent Office Office européen des brevets (11) EP 0 816 321 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.7: C07C 45/74, C07C 45/62, of the grant of the patent: C07C 45/73, C07C 49/04, 05.06.2002 Bulletin 2002/23 C07C 49/203, C07C 33/03 (21) Application number: 97111203.2 (22) Date of filing: 03.07.1997 (54) Process for producing 6-methyl-2-heptanone analogues, and process for producing phyton and isophytol Verfahren zur Herstellung von 6-Methyl-2-Heptanon Analogen, und Verfahren zur Herstellung von Phyton und Isophytol Procédé pour la préparation d’analogues de 6-méthyl-2-heptanone, et procédé pour la préparation de phytone et d’isophytol (84) Designated Contracting States: (56) References cited: AT BE CH DE FR GB IT LI NL EP-A- 0 008 741 EP-A- 0 022 955 EP-A- 0 765 853 DE-C- 823 291 (30) Priority: 05.07.1996 JP 19548096 US-A- 2 485 989 US-A- 2 499 172 11.12.1996 JP 35221496 US-A- 2 809 215 06.03.1997 JP 5135697 • R. HEILMANN ET AL.: "Recherches sur les (43) Date of publication of application: cétones éthyléniques. - V. Isomérie cis-trans 07.01.1998 Bulletin 1998/02 dans les cétones du type R.CH=CH.CO.CH3" BULLETIN DE LA SOCIETE CHIMIQUE DE (60) Divisional application: FRANCE., 1957, PARIS FR, pages 112-118, 01109535.3 / 1 122 236 XP002043076 • M. MOUSSERON-CANET ET AL.: "Vitesses (73) Proprietor: KURARAY CO., LTD.
    [Show full text]
  • Plastid Gene Expression and Plant Development Require a Plastidic Protein of the Mitochondrial Transcription Termination Factor Family
    Plastid gene expression and plant development require a plastidic protein of the mitochondrial transcription termination factor family Elena Babiychuka,b, Klaas Vandepoelea,b, Josef Wissingc, Miguel Garcia-Diazd, Riet De Ryckea,b, Hana Akbarie, Jérôme Joubèsf, Tom Beeckmana,b, Lothar Jänschc, Margrit Frentzene, Marc C. E. Van Montagub,1, and Sergei Kushnira,b,1 aDepartment of Plant Systems Biology, VIB, 9052 Ghent, Belgium; bDepartment of Plant Biotechnology and Genetics, Ghent University, 9052 Ghent, Belgium; cAbteilung Zellbiologie, Helmholtz-Zentrum für Infektionsforschung GmbH, 38124 Braunschweig, Germany; dPharmacological Sciences, Stony Brook University, Stony Brook, NY 11794-8651; eInstitut für Biologie I, Spezielle Botanik, Rheinisch-Westfälische Technische Hochschule Aachen, 52056 Aachen, Germany; and fUniversité Victor Ségalen Bordeaux 2, Laboratoire de Biogenèse Membranaire, Centre National de la Recherche Scientifique, 33076 Bordeaux Cedex, France Contributed by Marc C. E. Van Montagu, March 3, 2011 (sent for review December 6, 2010) Plastids are DNA-containing organelles unique to plant cells. In fluence transcription (8). mTERF3 acts as a specific repressor of Arabidopsis, one-third of the genes required for embryo devel- mammalian mtDNA transcription initiation in vivo (9). opment encode plastid-localized proteins. To help understand the Here, we show that 11 of 35 annotated Arabidopsis mTERFs role of plastids in embryogenesis and postembryonic develop- are targeted to plastids. Genetic complementation indicated that ment, we characterized proteins of the mitochondrial transcrip- early embryo arrest is a characteristic phenotype of mutation in tion termination factor (mTERF) family, which in animal models, mTERF/At4g02990, whereas in vitro cell culture and analysis of comprises DNA-binding regulators of mitochondrial transcription.
    [Show full text]