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(12) United States Patent (10) Patent No.: US 7,858,378 B2 Yabuki Et Al

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(12) United States Patent (10) Patent No.: US 7,858,378 B2 Yabuki Et Al US007858378B2 (12) United States Patent (10) Patent No.: US 7,858,378 B2 Yabuki et al. (45) Date of Patent: Dec. 28, 2010 (54) METHOD FOR THE DETERMINATION OF Cysteine Precursors by a C-S Lyase Isolated from Axilla bacteria, BODY ODOR Chemistry & Biodiversity, 2004, vol. 1, pp. 1058-1067.* Hendriks et al., Feline: A Urinary Amino Acid of Felidae, Comp. (75) Inventors: Masayuki Yabuki, Sumida-ku (JP); Biochem. Physiol., 1995, vol. 1128, pp. 581-588.* Yoshihiro Hasegawa, Sumida-ku (JP); Wouter H. Hendriks, et al., “Felinine: A Urinary Amino Acid of Shun Nakamura, Haga-gun (JP) Felidale'. Comp. Biochem. Physiol...vol. 112B, pp. 581–588, 1995. (73) Assignee: Kao Corporation, Tokyo (JP) Natsch, Andreas et al., Identification of Odoriferous Sulfanylalkanois in Human Azilla Secretions and Their Formation through Cleavage of (*) Notice: Subject to any disclaimer, the term of this Cysteine Precursors by a C-S Lyase Isolated from Axilla bacteria, patent is extended or adjusted under 35 Chemistry & Biodiversity, 2004, vol. 1, pp. 1058-1067. U.S.C. 154(b) by 0 days. Starkenmann, Christian et al., Identificiation of the Precursor of (S)- 3-Menthyl-3-sulfanylhexan-1-ol, the Sulfury Malodor of Human (21) Appl. No.: 12/537,034 Axilla Sweat, Chemistry & Biodiversity, 2005, vol. 2, pp. 705-716. (22) Filed: Aug. 6, 2009 * cited by examiner (65) Prior Publication Data Primary Examiner Walter D Griffin Assistant Examiner Christine T. Mui US 201O/OO35355A1 Feb. 11, 2010 (74) Attorney, Agent, or Firm Oblon, Spivak, McClelland, Maier & Neustadt, L.L.P. Related U.S. Application Data (62) Division of application No. 11/568,778, filed as appli (57) ABSTRACT cation No. PCT/JP2005/007835 on Apr. 25, 2005, now Pat. No. 7,608,459. A method for determining potential for body odor and a (30) Foreign Application Priority Data method for determining the effectiveness of a deodorant car May 11, 2004 (JP) ............................. 2004-141244 ried out by detecting a substance represented by the following formula (1) or a derivative thereof: (51) Int. Cl. GOIN33/50 (2006.01) Formula 1 C07C 229/02 (2006.01) NH2 GOIN 33/48 (2006.01) GOIN33/00 (2006.01) OH (52) U.S. Cl. ....................................... 436/111; 562/556 (58) Field of Classification Search ................. 436/111; 562/556 See application file for complete search history. (56) References Cited FOREIGN PATENT DOCUMENTS JP 2001 220593 8, 2001 wherein R' is a hydrogen atom or a methyl group, R is an JP 2001 271088 10, 2001 alkyl group containing 1 to 5 carbon atoms, and R is a OTHER PUBLICATIONS hydrogen atom or a methyl group. Natsch, Andreas et al., Identification of Odoriferous Sulfanylalkanols in Human Azilla Secretions and Their Formation through Cleavage of 11 Claims, 8 Drawing Sheets U.S. Patent Dec. 28, 2010 Sheet 1 of 8 US 7,858,378 B2 Fig. IA 3. i e U.S. Patent Dec. 28, 2010 Sheet 2 of 8 US 7,858,378 B2 Fig. IB 3. 2 s S 1065138 U.S. Patent Dec. 28, 2010 Sheet 3 of 8 US 7,858,378 B2 Fig. IC d e A. U.S. Patent Dec. 28, 2010 Sheet 4 of 8 US 7,858,378 B2 FIG. 2A 3.26 t f'2ss,rv | ar-332 6. - \-3:44.522558wr----- (91-51848-393-338&tiss 129-1425-- a----- d 15e9. h s E Oes 5. DeB 7 B Time, min U.S. Patent Dec. 28, 2010 Sheet 5 of 8 US 7,858,378 B2 A.0. 8 6 t 3,066 S 2.O e6 58-99-8---------- U.S. Patent Dec. 28, 2010 Sheet 6 of 8 US 7,858,378 B2 FIG. 2C 2.TeS 25es 2es Oes 5.SSS. U.S. Patent Dec. 28, 2010 Sheet 7 of 8 US 7,858,378 B2 FIG. 3A U.S. Patent Dec. 28, 2010 Sheet 8 of 8 US 7,858,378 B2 FIG. 3B US 7,858,378 B2 1. 2 METHOD FOR THE DETERMINATION OF ant is mixed with the sweat collected from the armpit of the BODY ODOR test subject, and the smell of the mixture is evaluated after an adequate incubation of the mixture. FIELD OF THE INVENTION Both of these methods, however, are associated with the considerable burden of the test subjects and this leads to the This invention relates to a method for determination of the difficulty of evaluating a large number of candidate deodor possibility of body odor generation, and in particular, apo ants under the same conditions. In addition, quantitative crine odor generation. This invention also relates to a method assessment is difficult due to the large margin of the Subjec for determination of the effectiveness of a deodorant. tive decision of the panelist and assessment error due to 10 olfactory fatigue. Furthermore, such method is associated BACKGROUND OF THE INVENTION with the difficulty in differentiating whether it was the gen eration of the apocrine odor that was suppressed by the can With the recent increase in hygiene consciousness, an didate deodorant; whether the apocrine odor that had been increasing number of people are concerned about their body generated was deodorized; or whether the apocrine odor was odor. The term “body odor’ is a generic term for the odor or 15 sensed to a lower degree by the presence of another odor. Smell generated in various parts of the body, and main sources Accordingly, an accurate, efficient, objective, and quantita of the odor or Smell include the head, mouth, armpit, groin, tive determination of the “effectiveness in suppressing the and foot sole. Among such sources of the odor or Smell, the apocrine odor generation' has been difficult. armpit smell is easily detected by the person himself/herself The inventors of the present invention investigated odor or by the people in the immediate area of the person, and the components in the human armpit, and found that the main factors such as presence/absence, strength, and qualitative components responsible for the apocrine odor are alcohol difference of the armpit smell greatly affect the systemic body compounds having a thiol group at position 3 (hereinafter odor. Therefore, it is often the armpit smell and not the body Sometimes referred to as 3-mercapto alcohol compound) as odor in general that is annoying for the person himself/herself typically represented by 3-mercapto-3-methylhexane-1-ol. or for the people in the immediate area of the person. 25 3-mercaptohexane-1-ol. 3-mercaptopentane-1-ol. 3-mer The armpit Smell comprises a sour and stuffy Smell and a capto-2-methylbutane-1-ol, and 3-mercapto-2-methylpen smell specifically found in the armpit. The sour and stuffy tane-1-ol (Non-patent document 1). Smell is generated by decomposition of the eccrine Sweat and The inventors of the present invention also found that grime secreted by the eccrine gland by the action of the 3-mercapto-3-methylhexane-1-ol is present at a mass ratio of indigenous bacteria of the skin. The main cause of this Smell 30 10 or more times higher than that of other 3-mercapto alcohol is lower carboxylic acids containing 2 to 5 carbonatoms, and compounds, and that this 3-mercapto-3-methyl-hexane-1-ol this smell is called a “lower fatty acid smell”, or more simply, is the most common 3-mercapto alcohol compound in the an “acid smell”. In contrast, the smell specific to the armpit is armpit of people having apocrine odor (Non-patent document generated by decomposition of apocrine Sweat Secreted from 1). the apocrine gland containing proteins and cholesterol at a 35 The inventors of the present invention also found that the high concentration by the action of the indigenous bacteria of 3-mercapto-3-methylhexane-1-ol is an optically active Sub the skin, and this smell is called the “apocrine odor or “arm stance comprising 72% by mass of (S)-3-mercapto-3-meth pit smell' (hereinafter referred to as the "apocrine odor). ylhexane-1-ol and 28% by mass of (R)-3-mercapto-3-meth Accordingly, for those people who are conscious about ylhexane-1-ol (Non-patent document 1) their body odor, and in particular, the armpit smell, it would 40 Patent Document 1 discloses that, as flavoring compo be quite important to know the degree of their apocrine odor nents, 3-mercapto-2-methylbutane-1-ol has the characteristic that they originally have in their armpit, and whether their odor like grass, leek, orgas, (S)-3-mercaptohexane-1-ol has a own effort of reducing the body odor, for example, by the use grass or rustic odor, and (R)-3-mercaptohexane-1-ol has odor of deodorant products or Surgical removal of the apocrine like a grapefruit/passion fruit, gooseberry, or onion. gland, actually had some effects. 45 Conventional methods that have been used in finding the Non-patent document 1 Japanese Journal of Taste and degree (presence or strength) of one's own apocrine odor in Smell Research, vol. 10, No. 3, pages 807-810 (December the armpit include (1) a sensory test in which the armpit Smell 2003). is evaluated by a third person, (2) an estimation based on Patent Document 1 JP-A-2001-2634. information Such as the presence of a person with the armpit 50 Smell in his or her family and moist cerumen, and the like DISCLOSURE OF THE INVENTION which are said to be related to the apocrine odor. However, the method (1) is associated with the difficulty of The present invention has enabled an objective and quan a quantitative assessment due to the large margin of the Sub titative determination of the body odor, and in particular, jective decision of the panelist and assessment error due to 55 latent apocrine odor, namely, the possibility (potential) of olfactory fatigue.
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