3-Mercapto-3-methylbutan-1-ol

3-Mercapto-3-methylbutan-1-ol[1]
Names
Preferred IUPAC name
3-Methyl-3-sulfanylbutan-1-ol
Other names
3-Mercapto-3-methylbutan-1-ol (no longer recommended[2])
Identifiers
3D model (JSmol)
Abbreviations MMB
ChEBI
ChemSpider
ECHA InfoCard 100.157.543 Edit this at Wikidata
EC Number
  • 629-355-5
UNII
  • InChI=1S/C5H12OS/c1-5(2,7)3-4-6/h6-7H,3-4H2,1-2H3 checkY
    Key: GBCGIJAYTBMFHI-UHFFFAOYSA-N checkY
  • InChI=1/C5H12OS/c1-5(2,7)3-4-6/h6-7H,3-4H2,1-2H3
    Key: GBCGIJAYTBMFHI-UHFFFAOYAN
  • CC(C)(CCO)S
  • OCCC(S)(C)C
Properties
C5H12OS
Molar mass 120.21 g/mol
Density 0.985 g/mL at 20 °C
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H315, H318, H319, H335
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

3-Mercapto-3-methylbutan-1-ol, also known as MMB, is a common odorant found in food and cat urine. The aromas ascribed to MMB include catty,[3] roasty, broth-like, meaty, and savory,[4] or similar to cooked leeks.[5]

MMB is an organosulfur compound with the formula C5H12OS. Its structure consists of isopentane with a primary alcohol group and a tertiary thiol group attached to a β-carbon relative to the alcohol. MMB is found in the urine of leopards and domestic cats, and is considered an important semiochemical in male scent-marking.[6] MMB is also a common odorant in food, including coffee,[7] passionfruit juice,[8] and Sauvignon Blanc wines.[5] As a tertiary thiol, MMB is structurally similar to other "catty" thiols, including 3-mercapto-3-methyl-2-pentanone, 4-mercapto-4-methyl-2-pentanone, 8-mercapto-p-menthan-3-one, and 2-mercapto-2-methylbutane.[4]

  1. ^ 3-Mercapto-3-methylbutan-1-ol at Sigma-Aldrich
  2. ^ Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 697. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. The prefixes 'mercapto' (–SH), and 'hydroseleno' or selenyl (–SeH), etc. are no longer recommended.
  3. ^ A. Buettner (April 27, 2002). "Influence of Human Salivary Enzymes on Odorant Concentration Changes Occurring in Vivo. 1. Esters and Thiols". J. Agric. Food Chem. 50 (11): 3283–3289. doi:10.1021/jf011586r. PMID 12009999.
  4. ^ a b M. Rychlik; P. Schieberle; W. Grosch (1998). Compilation of odor thresholds, odor qualities and retention indices of key food odorants. Instit für Lebensmittelchemie der Technischen Universität München, Garching. OCLC 59392244.
  5. ^ a b T. Tominaga; A. Furrer; R. Henry; D. Dubourdieu (December 4, 1998). "Identification of new volatile thiols in the aroma of Vitis vinifera L. var. sauvignon blanc wines". Flavour and Fragrance Journal. 13 (3): 159–162. doi:10.1002/(SICI)1099-1026(199805/06)13:3<159::AID-FFJ709>3.0.CO;2-7. Archived from the original (pdf) on December 16, 2012.
  6. ^ P. Apps; M. Claase; B. Yexley & J. McNutt (2017). "Interspecific responses of wild African carnivores to odour of 3-mercapto-3-methylbutanol, a component of wildcat and leopard urine". J. Ethol. 35 (2): 153–159. doi:10.1007/s10164-016-0503-7.
  7. ^ C. Masanetz; I. Blank & W. Grosch (1995). "Synthesis of [H6]-3-Mercapto-3-methylbutyl Formate to be used as an Internal Standard in Quantification Assays". Flavour Fragr. J. 10: 9–14. doi:10.1002/ffj.2730100103.
  8. ^ T. Tominaga & D. Dubourdieu (June 2000). "Identification of Cysteinylated Aroma Precursors of Certain Volatile Thiols in Passion Fruit Juice". J. Agric. Food Chem. 48 (7): 2874–2876. doi:10.1021/jf990980a. PMID 10898639.