Showing Compound alpha-fenchyl alcoholalpha-1,3,3-trimethyl-norbornan-2-ol (FDB029688)

Record Information

Version

1.0

Creation date

2011-09-26 22:54:23 UTC

Update date

2020-09-17 15:31:22 UTC

Primary ID

FDB029688

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

alpha-fenchyl alcoholalpha-1,3,3-trimethyl-norbornan-2-ol

Description

Fenchol or 1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Fenchol is a naturally occurring bicyclic monoterpenoid and an isomer of Borneol. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclation reactions to yield a diverse number of cyclic arrangements. Fenchol is an extremely weak basic (essentially neutral) compound (based on its pKa). It is a colorless or white solid with a characteristic scent found in basil and Aster. Fenchol is used extensively in perfumery.

CAS Number

14575-74-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(-)-a-Fenchyl alcohol	Generator
(-)-alpha-Fenchol	PhytoBank
(-)-alpha-Fenchyl alcohol	Kegg
(-)-endo-Fenchol	PhytoBank
(-)-α-Fenchol	PhytoBank
(-)-Α-fenchyl alcohol	Generator
(1S,2-endo)-1,3,3-Trimethylnorbornan-2-ol	ChEBI
(1S,2S,4R)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol	PhytoBank
(1S,2S,4R)-endo-Fenchol	ChEBI
(1S-endo)-Fenchol	PhytoBank

Showing 1 to 10 of 41 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.87 g/L	ALOGPS
logP	2.3	ALOGPS
logP	2.15	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	-0.52	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	45.16 m³·mol⁻¹	ChemAxon
Polarizability	18.52 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

C10H18O

IUPAC name

(1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol

InChI Identifier

InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m1/s1

InChI Key

IAIHUHQCLTYTSF-MRTMQBJTSA-N

Isomeric SMILES

[H][C@@]1(O)C(C)(C)[C@]2([H])CC[C@@]1(C)C2

Average Molecular Weight

154.253

Monoisotopic Molecular Weight

154.1357652

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
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

carbobicyclic compound (CHEBI:15405 )
fenchane monoterpenoid (CHEBI:15405 )
Bicyclic monoterpenoids (LMPR0102120005 )

Ontology

No ontology term

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	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	alpha-fenchyl alcoholalpha-1,3,3-trimethyl-norbornan-2-ol, 1 TMS, 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	splash10-052r-0900000000-d82ad081287ed2639925	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-1900000000-94ea34fa991c83d8e3fa	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aca-9400000000-7d93799774481e0cda42	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-53ad86f1876aae2ee067	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-747f855f1574c214338c	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fe0-0900000000-2389c65fe686d8639bb1	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-3900000000-4094f7230adb483cf7e5	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a5c-6900000000-aabed757c552780da472	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053i-9600000000-6fa6ff11a1ac49887bb3	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-d2363ae8d4dbdcccda80	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-d2363ae8d4dbdcccda80	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0900000000-459bafe52d5b103e88a6	2021-10-21	View Spectrum

NMR

Not Available

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

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

14575-74-7

GoodScent ID

rw1551681

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
camphor	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

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Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference