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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.
2016-08-21
Determination of accurate electron chiral asymmetries in fenchone and camphor in the VUV range: sensitivity to isomerism and enantiomeric purity.
2016-05-14
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 Mon Mar 31 18:37:01 GMT 2025
Edited
by admin
on Mon Mar 31 18:37:01 GMT 2025
Record UNII
S436YKU51N
Record Status Validated (UNII)
Record Version
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Name Type Language
FENCHONE, (+)-
Common Name English
D-FENCHONE
FHFI   MI  
Preferred 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
(+)-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 Mon Mar 31 18:37:01 GMT 2025 , Edited by admin on Mon Mar 31 18:37:01 GMT 2025
JECFA EVALUATION D-FENCHONE
Created by admin on Mon Mar 31 18:37:01 GMT 2025 , Edited by admin on Mon Mar 31 18:37:01 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID60858862
Created by admin on Mon Mar 31 18:37:01 GMT 2025 , Edited by admin on Mon Mar 31 18:37:01 GMT 2025
PRIMARY
EVMPD
SUB13826MIG
Created by admin on Mon Mar 31 18:37:01 GMT 2025 , Edited by admin on Mon Mar 31 18:37:01 GMT 2025
PRIMARY
CHEBI
165
Created by admin on Mon Mar 31 18:37:01 GMT 2025 , Edited by admin on Mon Mar 31 18:37:01 GMT 2025
PRIMARY
CAS
4695-62-9
Created by admin on Mon Mar 31 18:37:01 GMT 2025 , Edited by admin on Mon Mar 31 18:37:01 GMT 2025
PRIMARY
JECFA MONOGRAPH
1395
Created by admin on Mon Mar 31 18:37:01 GMT 2025 , Edited by admin on Mon Mar 31 18:37:01 GMT 2025
PRIMARY
SMS_ID
100000078736
Created by admin on Mon Mar 31 18:37:01 GMT 2025 , Edited by admin on Mon Mar 31 18:37:01 GMT 2025
PRIMARY
PUBCHEM
1201521
Created by admin on Mon Mar 31 18:37:01 GMT 2025 , Edited by admin on Mon Mar 31 18:37:01 GMT 2025
PRIMARY
ECHA (EC/EINECS)
225-160-0
Created by admin on Mon Mar 31 18:37:01 GMT 2025 , Edited by admin on Mon Mar 31 18:37:01 GMT 2025
PRIMARY
CHEBI
4999
Created by admin on Mon Mar 31 18:37:01 GMT 2025 , Edited by admin on Mon Mar 31 18:37:01 GMT 2025
PRIMARY
MERCK INDEX
m5270
Created by admin on Mon Mar 31 18:37:01 GMT 2025 , Edited by admin on Mon Mar 31 18:37:01 GMT 2025
PRIMARY Merck Index
FDA UNII
S436YKU51N
Created by admin on Mon Mar 31 18:37:01 GMT 2025 , Edited by admin on Mon Mar 31 18:37:01 GMT 2025
PRIMARY