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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H16O
Molecular Weight 152.2334
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FENCHONE, (+)-

SMILES

CC1(C)[C@@H]2CC[C@@](C)(C2)C1=O

InChI

InChIKey=LHXDLQBQYFFVNW-XCBNKYQSSA-N
InChI=1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3/t7-,10+/m1/s1

HIDE SMILES / InChI

Molecular Formula C10H16O
Molecular Weight 152.2334
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

(+)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Foeniculum vulgare. This component has camphoraceous fragrance. (+)-Fenchone is used as a food flavour and in perfumes. Although, there are report that (+)-fenchone has toxic. P450 enzymes are shown to detoxify and/or toxify these compounds to metabolites more polar and sometimes more reactive metabolites. (+)-fenchone are oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives in human liver microsomes. CYP2A6 is suggested to be a principal enzyme in catalyzing (+)-fenchone 6-exo and 6-endo hydroxylation by human liver microsomes. 10-Hydroxylation of (+)-fenchone is also metabolized by CYP2B6.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Structure of fenchone by broadband rotational spectroscopy.
2016 Aug 21
Determination of accurate electron chiral asymmetries in fenchone and camphor in the VUV range: sensitivity to isomerism and enantiomeric purity.
2016 May 14
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
(+)-Fenchone hydroxylation activities by P450 enzymes were determined as follows. Standard reaction mixture contained human liver microsomes (0.1 mg/ml) or recombinant P450 (10 pmol/ml) with 100 uM concentration of (+)-fenchone in a final volume of 0.5 ml of 100 mM potassium phosphate buffer (pH 7.4) containing an NADPH-generating system consisting of 0,5 mM NADP+, 5 mM glucose 6-phosphate, and 0.5 unit of glucose 6-phosphate dehydrogenase/ml. The organic phase was transferred to an insert for analysis by gas chromatography-mass spectrometry. CYP2A6 and CYP2B6 in human liver microsomes were major enzymes involved in the hydroxylation of (+)-fenchone.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:50:35 UTC 2023
Edited
by admin
on Fri Dec 15 16:50:35 UTC 2023
Record UNII
S436YKU51N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FENCHONE, (+)-
Common Name English
Fenchone [WHO-DD]
Common Name English
D-1,3,3-TRIMETHYL-2-NORBORNANONE
Common Name English
D-FENCHONE [FHFI]
Common Name English
D-FENCHONE [MI]
Common Name English
FENCHONE
WHO-DD  
Common Name English
FEMA NO. 2479
Code English
D-FENCHONE
FHFI   MI  
Common Name English
(+)-FENCHONE [FCC]
Common Name English
(+)-FENCHONE
FCC  
Common Name English
2-NORBORNANONE, 1,3,3-TRIMETHYL-, (1S,4R)-(+)-
Systematic Name English
FENCHONE, D-
Common Name English
(1S)-1,3,3-TRIMETHYLBICYCLO(2.2.1)HEPTAN-2-ONE
Systematic Name English
BICYCLO(2.2.1)HEPTAN-2-ONE, 1,3,3-TRIMETHYL-, (1S,4R)-
Systematic Name English
Classification Tree Code System Code
CFR 21 CFR 172.515
Created by admin on Fri Dec 15 16:50:35 UTC 2023 , Edited by admin on Fri Dec 15 16:50:35 UTC 2023
JECFA EVALUATION D-FENCHONE
Created by admin on Fri Dec 15 16:50:35 UTC 2023 , Edited by admin on Fri Dec 15 16:50:35 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID60858862
Created by admin on Fri Dec 15 16:50:35 UTC 2023 , Edited by admin on Fri Dec 15 16:50:35 UTC 2023
PRIMARY
EVMPD
SUB13826MIG
Created by admin on Fri Dec 15 16:50:35 UTC 2023 , Edited by admin on Fri Dec 15 16:50:35 UTC 2023
PRIMARY
CHEBI
165
Created by admin on Fri Dec 15 16:50:35 UTC 2023 , Edited by admin on Fri Dec 15 16:50:35 UTC 2023
PRIMARY
CAS
4695-62-9
Created by admin on Fri Dec 15 16:50:35 UTC 2023 , Edited by admin on Fri Dec 15 16:50:35 UTC 2023
PRIMARY
JECFA MONOGRAPH
1395
Created by admin on Fri Dec 15 16:50:35 UTC 2023 , Edited by admin on Fri Dec 15 16:50:35 UTC 2023
PRIMARY
SMS_ID
100000078736
Created by admin on Fri Dec 15 16:50:35 UTC 2023 , Edited by admin on Fri Dec 15 16:50:35 UTC 2023
PRIMARY
PUBCHEM
1201521
Created by admin on Fri Dec 15 16:50:35 UTC 2023 , Edited by admin on Fri Dec 15 16:50:35 UTC 2023
PRIMARY
ECHA (EC/EINECS)
225-160-0
Created by admin on Fri Dec 15 16:50:35 UTC 2023 , Edited by admin on Fri Dec 15 16:50:35 UTC 2023
PRIMARY
CHEBI
4999
Created by admin on Fri Dec 15 16:50:35 UTC 2023 , Edited by admin on Fri Dec 15 16:50:35 UTC 2023
PRIMARY
MERCK INDEX
m5270
Created by admin on Fri Dec 15 16:50:35 UTC 2023 , Edited by admin on Fri Dec 15 16:50:35 UTC 2023
PRIMARY Merck Index
FDA UNII
S436YKU51N
Created by admin on Fri Dec 15 16:50:35 UTC 2023 , Edited by admin on Fri Dec 15 16:50:35 UTC 2023
PRIMARY