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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:43:00 UTC
Update Date2019-07-23 06:19:18 UTC
HMDB IDHMDB0035703
Secondary Accession Numbers
  • HMDB35703
Metabolite Identification
Common Namep-Menth-1-ene-8-thiol
Descriptionp-Menth-1-ene-8-thiol, also known as 8-mercapto-p-menth-1-ene or fema 3700, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. p-Menth-1-ene-8-thiol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862758
Synonyms
ValueSource
1-p-Menthen-8-thiolHMDB
1-p-Menthene-8-thiolHMDB
4-(1-Mercapto-1-methylethyl)-1-methylcyclohexeneHMDB
8-Mercapto-p-menth-1-eneHMDB
a,a,4-Trimethyl-3-cyclohexene-1-methanethiol, 9ciHMDB
alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanethiolHMDB
alpha,alpha,4-Trimethylcyclohex-3-ene-1-methanethiolHMDB
FEMA 3700HMDB
p-1-Menthen-8-thiolHMDB
p-1-Menthene-8-thiolHMDB
p-Menth-1-en-8-thiolHMDB
Chemical FormulaC10H18S
Average Molecular Weight170.315
Monoisotopic Molecular Weight170.112921266
IUPAC Name2-(4-methylcyclohex-3-en-1-yl)propane-2-thiol
Traditional Namegrapefruit mercaptan
CAS Registry Number71159-90-5
SMILES
CC1=CCC(CC1)C(C)(C)S
InChI Identifier
InChI=1S/C10H18S/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3
InChI KeyZQPCOAKGRYBBMR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Alkylthiol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.03 g/LALOGPS
logP4.46ALOGPS
logP3.22ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.96ChemAxon
pKa (Strongest Basic)-9.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity54.59 m³·mol⁻¹ChemAxon
Polarizability20.89 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05r0-9300000000-4b504904330731dff6ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-2900000000-e324b040fccb0aee237dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-9700000000-cd48ced934c3de5ce660Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uyi-9300000000-9f468e08580445f87f5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014r-0900000000-a781d35783d8952c0a40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-0900000000-85224798377d96baf79dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9500000000-c8c1276ccc91d6617a5cSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014423
KNApSAcK IDNot Available
Chemspider ID4932553
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6427135
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.