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

Record Information

Version

1.0

Creation date

2010-04-08 22:10:58 UTC

Update date

2019-11-26 03:09:15 UTC

Primary ID

FDB013900

Secondary Accession Numbers

FDB013899

Chemical Information

FooDB Name

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

Description

Dihydroactinidiolide 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 Number

17092-92-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(S)-5,6,7,7a-Tetrahydro-4,4,7a-trimethyl-2(4H)-benzofuranone	Generator
(S)-5,6,7,7Α-tetrahydro-4,4,7α-trimethyl-2(4H)-benzofuranone	Generator
2-Hydroxy-2,6,6-trimethylcyclohexylidene-1-acetic acid lactone	HMDB
2-Hydroxy-2,6,6-trimethylcyclohexylideneacetic acid gamma-lactone	MeSH, HMDB
4,4,7a-Trimethyl-5,6,7,7a-tetrahydro-4H-benzofuran-2-one	HMDB
4,5,7,7a-tetrahydro-4,4,7a-Trimethyl-2(6H)benzofuranone	HMDB
5,6,7,7a-Tetrahydro-4,4,7a-trimethyl-2(4H)-benzofuranone	biospider
Dihydroactindiolide	biospider

Showing 1 to 8 of 8 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.61 g/L	ALOGPS
logP	3.28	ALOGPS
logP	2.57	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	50.93 m³·mol⁻¹	ChemAxon
Polarizability	19.89 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C11H16O2

IUPAC name

4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one

InChI Identifier

InChI=1S/C11H16O2/c1-10(2)5-4-6-11(3)8(10)7-9(12)13-11/h7H,4-6H2,1-3H3

InChI Key

IMKHDCBNRDRUEB-UHFFFAOYSA-N

Isomeric SMILES

CC12CCCC(C)(C)C1=CC(=O)O2

Average Molecular Weight

180.2435

Monoisotopic Molecular Weight

180.115029756

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

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 Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant:

Coffea

Role

Industrial application:

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 73.30%; H 8.95%; O 17.75%	DFC
Melting Point	Mp 71-72° (40-41°)	DFC
Optical Rotation	[a]22D +122.7 (CHCl3) (synthetic)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-03di-5900000000-875f4155f7a4044b0a2a	2015-03-01	View Spectrum
Predicted GC-MS	Dihydroactinidiolide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-007c-6900000000-27116463eaa31cd838f5	Spectrum
Predicted GC-MS	Dihydroactinidiolide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-b0a7c2689f1ca5d0ae35	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-4900000000-9f6cefae5043b00a2ca8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00l6-9000000000-ea0ae11d0ba2410fe44c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-71187b755914bfd750bf	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004r-0900000000-e3790c89f994eda416fc	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05nr-2900000000-c550c1933884677823ea	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-ed614b6bd089f6f9641a	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fb9-0900000000-732e641af33d2bb8a042	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-a68e0eac4bebe698e071	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-fa414fe3da96b61b2fda	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-3900000000-a38dd3a7eff08112fb9a	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9500000000-f3a71ce8b3e13f563ab8	2021-09-25	View Spectrum

NMR

Type	Description		View

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

JJR15-S:JJR17-U

EAFUS ID

Not Available

Dr. Duke ID

DIHYDROACTINIDIOLIDE

BIGG ID

Not Available

KNApSAcK ID

C00000319

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1547981

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
coumarin	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
musk	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Showing 1 to 2 of 2 entries

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).