Back to Compounds

Showing Compound (S)-5,6,7,7alpha-Tetrahydro-4,4,7alpha-trimethyl-2(4H)-benzofuranone (FDB013900)

Record Information
Version1.0
Creation date2010-04-08 22:10:58 UTC
Update date2019-11-26 03:09:15 UTC
Primary IDFDB013900
Secondary Accession Numbers
  • FDB013899
Chemical Information
FooDB Name(S)-5,6,7,7alpha-Tetrahydro-4,4,7alpha-trimethyl-2(4H)-benzofuranone
DescriptionDihydroactinidiolide is a member of the class of compounds known as benzofurans. Benzofurans are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Dihydroactinidiolide is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Dihydroactinidiolide is a red fruit, ripe apricot, and woody tasting compound found in coffee and coffee products, fruits, and tea, which makes dihydroactinidiolide a potential biomarker for the consumption of these food products. Dihydroactinidiolide exists in all eukaryotes, ranging from yeast to humans. Dihydroactinidiolide is a volatile terpene. It has a sweet, tea-like odor and is used as a fragrance. Dihydroactinidiolide occurs naturally in black tea, fenugreek, fire ants, mangos, silver vine (Actinidia polygama), and tobacco. It has also been prepared synthetically .
CAS Number17092-92-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-Hydroxy-2,6,6-trimethylcyclohexylidene-1-acetic acid lactoneHMDB
4,4,7a-Trimethyl-5,6,7,7a-tetrahydro-4H-benzofuran-2-oneHMDB
4,5,7,7a-tetrahydro-4,4,7a-Trimethyl-2(6H)benzofuranoneHMDB
2-Hydroxy-2,6,6-trimethylcyclohexylideneacetic acid gamma-lactoneMeSH, HMDB
(S)-5,6,7,7a-Tetrahydro-4,4,7a-trimethyl-2(4H)-benzofuranoneGenerator
(S)-5,6,7,7Α-tetrahydro-4,4,7α-trimethyl-2(4H)-benzofuranoneGenerator
5,6,7,7a-Tetrahydro-4,4,7a-trimethyl-2(4H)-benzofuranonebiospider
Dihydroactindiolidebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.61 g/LALOGPS
logP3.28ALOGPS
logP2.57ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity50.93 m³·mol⁻¹ChemAxon
Polarizability19.89 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H16O2
IUPAC name4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one
InChI IdentifierInChI=1S/C11H16O2/c1-10(2)5-4-6-11(3)8(10)7-9(12)13-11/h7H,4-6H2,1-3H3
InChI KeyIMKHDCBNRDRUEB-UHFFFAOYSA-N
Isomeric SMILESCC12CCCC(C)(C)C1=CC(=O)O2
Average Molecular Weight180.2435
Monoisotopic Molecular Weight180.115029756
Classification
Description Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassNot Available
Direct ParentBenzofurans
Alternative Parents
Substituents
  • Benzofuran
  • 2-furanone
  • Dihydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 73.30%; H 8.95%; O 17.75%DFC
Melting PointMp 71-72° (40-41°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]22D +122.7 (CHCl3) (synthetic)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-03di-5900000000-875f4155f7a4044b0a2a2015-03-01View Spectrum
Predicted GC-MSDihydroactinidiolide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-007c-6900000000-27116463eaa31cd838f5Spectrum
Predicted GC-MSDihydroactinidiolide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-b0a7c2689f1ca5d0ae352016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-4900000000-9f6cefae5043b00a2ca82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l6-9000000000-ea0ae11d0ba2410fe44c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-71187b755914bfd750bf2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-0900000000-e3790c89f994eda416fc2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05nr-2900000000-c550c1933884677823ea2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-ed614b6bd089f6f9641a2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-0900000000-732e641af33d2bb8a0422021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-a68e0eac4bebe698e0712021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-fa414fe3da96b61b2fda2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3900000000-a38dd3a7eff08112fb9a2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9500000000-f3a71ce8b3e13f563ab82021-09-25View Spectrum
NMR
TypeDescriptionView
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJJR15-S:JJR17-U
EAFUS IDNot Available
Dr. Duke IDDIHYDROACTINIDIOLIDE
BIGG IDNot Available
KNApSAcK IDC00000319
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1547981
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
musk
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
coumarin
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).