AFCDB: Fenchone (FDB014519)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:19 UTC

Update date

2019-11-26 03:10:16 UTC

Primary ID

FDB014519

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Fenchone

Description

Fenchone is a natural organic compound classified as a monoterpene and a ketone. It is a colorless oily liquid. It has a structure and an odor similar to camphor. Fenchone is a constituent of absinthe and the essential oil of fennel. Fenchone is used as a flavor in foods and in perfumery. Only 2 stereoisomers are possible: D-fenchone (enantiomer 1S,4R is dextrogyre (+)) and L-fenchone (enantiomer 1R,4S is levogyre (-)). Due to the small size of the cycle, the 2 other diastereoisomers (1S4S and 1R4R) are not possible. [Wikipedia]. Fenchone is found in many foods, some of which are ceylon cinnamon, sweet basil, saffron, and dill.

CAS Number

1195-79-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.88 g/L	ALOGPS
logP	2.54	ALOGPS
logP	3.06	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	-7.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	44.54 m³·mol⁻¹	ChemAxon
Polarizability	17.85 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H16O

IUPAC name

1,3,3-trimethylbicyclo[2.2.1]heptan-2-one

InChI Identifier

InChI=1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3

InChI Key

LHXDLQBQYFFVNW-UHFFFAOYSA-N

Isomeric SMILES

CC1(C)C2CCC(C)(C2)C1=O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

Classification

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Fenchane monoterpenoid
Bicyclic monoterpenoid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

carbobicyclic compound (CHEBI:4999 )
cyclic terpene ketone (CHEBI:4999 )
fenchane monoterpenoid (CHEBI:4999 )
Bicyclic monoterpenoids (C11387 )
Cyclic monoterpenes (C11387 )
Bicyclic monoterpenoids (LMPR0102120016 )
a small molecule (CPD-13994 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 78.90%; H 10.59%; O 10.51%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-00lr-9000000000-0490bda5c76f7c0af3bd	2015-03-01	View Spectrum
GC-MS	(-)-Fenchone, non-derivatized, GC-MS Spectrum	splash10-001i-9000000000-39548fbec25228381f9b	Spectrum
GC-MS	(-)-Fenchone, non-derivatized, GC-MS Spectrum	splash10-001i-9000000000-a6f20ad638918f01e975	Spectrum
GC-MS	(-)-Fenchone, non-derivatized, GC-MS Spectrum	splash10-001i-9000000000-39548fbec25228381f9b	Spectrum
GC-MS	(-)-Fenchone, non-derivatized, GC-MS Spectrum	splash10-001i-9000000000-a6f20ad638918f01e975	Spectrum
GC-MS	(-)-Fenchone, non-derivatized, GC-MS Spectrum	splash10-00lr-9000000000-6be6cc8fad0feab50dc4	Spectrum
Predicted GC-MS	(-)-Fenchone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0043-9400000000-8a489af79633badeca62	Spectrum
Predicted GC-MS	(-)-Fenchone, 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	splash10-0udi-0900000000-24a8ed13cef6845f9bec	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-5900000000-48ac2ef18d27307d28a4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00or-9200000000-a262db5efd11c7793ea7	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-611d1944cb83d52bd473	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-aa8c9e54bea95cd3d999	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01c9-5900000000-7356fe255f32eabff21c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0900000000-2a5636c44361fc473306	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-2900000000-620886e230bbabe8a4ef	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ue9-5900000000-b24f702346175a6b0100	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0043-9200000000-42f567566720679e24e5	2021-09-24	View Spectrum

NMR

Type	Description		View

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

14525

Pubchem Substance ID

Not Available

ChEBI ID

4999

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

JRN54-N:JRN54-N

EAFUS ID

Not Available

Dr. Duke ID

ALPHA-FENCHONE|FENCHONE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Fenchone

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti Alzheimeran	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti cholinesterase	37733	An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).	DUKE
counterirritant			DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
secretolytic			DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

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).

Fenchone (FDB014519)

Structure for FDB014519 (Fenchone)