Showing Compound Cuminyl alcohol (FDB008492)

Record Information

Version

1.0

Creation date

2010-04-08 22:08:06 UTC

Update date

2020-09-17 15:36:12 UTC

Primary ID

FDB008492

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Cuminyl alcohol

Description

Cuminol or Cuminyl alcohol, also known as p-cumin-7-ol or 4-Isopropylbenzyl alcohol, belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. 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 (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Cuminol is an extremely weak basic (essentially neutral) compound (based on its pKa). Cuminol is an alcohol derivative of p-Cymene. It exists as a clear, colorless liquid that is poorly soluble in water. Cuminol can be used as a food additive or as a cosmetic fragrance. It has a cumin, caraway or spicy, herbal aroma and a similar spicy, herbal or peppery taste. Cuminol is found naturally in a number of plants, spices and foods including cumin seed and cumin oils, caraway eucalyptus oils, thyme, sunflowers, tuermeric, guava fruit and other spices and essential oils. Cumin, a widely used spice, is known to have anti-diabetic properties and two of its phytochemicals: cuminol and cuminaldehyde appear to be among the most active components. Cuminol is a potent insulinotrophic molecule that can enhance insulin secretion by up to 4-fold (in rat islet cells) (PMID: 23507295). It also exhibits strong beta-cell protective action (PMID: 23507295).

CAS Number

536-60-7

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(4-Isopropylphenyl)methanol	ChEBI
(4-Propan-2-ylphenyl)methanol	ChEBI
4-(1-Methylethyl)benzenemethanol	ChEBI
Cumic alcohol	ChEBI
Cumin alcohol	ChEBI
Cuminic alcohol	ChEBI
Cuminol	ChEBI
Cumyl alcohol	ChEBI
p-Cumic alcohol	ChEBI
p-Cumin-7-ol	ChEBI
p-Cymen-7-ol	ChEBI
p-Isopropylbenzyl alcohol	ChEBI
p-Mentha-1,3,5-trien-7-ol	ChEBI
Para-cymen-7-ol	ChEBI
4-Isopropylbenzyl alcohol	Kegg
4-(1-Methylethyl)-benzenemethanol	HMDB
4-(1-Methylethyl)benzene methanol	HMDB
4-(1-Methylethyl)benzenemethanol, 9ci	HMDB
4-Isopropyl benzyl alcohol	HMDB
4-ISOPROPYLBENZENEMETHANOL	HMDB
Cuminol ( P-cymen-7-ol)	HMDB
Cuminylalcohol	HMDB
FEMA 2933	HMDB
P-Cymen-7-ol, 8ci	HMDB
P-Cymene-7-ol	HMDB
P-Isopropyl benzyl alcohol	HMDB
P-Isopropyl-benzyl alcohol	HMDB
Cuminyl alcohol	ChEBI
4-(1-methylethyl)-benzenemethanol	biospider
4-(1-methylethyl)benzene methanol	biospider
4-(1-methylethyl)benzenemethanol	biospider
4-(1-Methylethyl)benzenemethanol, 9CI	db_source
Benzenemethanol, 4-(1-methylethyl)-	biospider
Benzyl alcohol, p-isopropyl-	biospider
cuminol ( p-cymen-7-ol)	biospider
P-cumic alcohol	biospider
p-Cymen-7-ol, 8CI	db_source
p-cymene-7-ol	biospider
P-isopropyl benzyl alcohol	biospider
para-Cymen-7-ol	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.65 g/L	ALOGPS
logP	2.63	ALOGPS
logP	2.45	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	15.05	ChemAxon
pKa (Strongest Basic)	-2.8	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	2	ChemAxon
Refractivity	47.06 m³·mol⁻¹	ChemAxon
Polarizability	17.98 Å³	ChemAxon
Number of Rings	1	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

C10H14O

IUPAC name

[4-(propan-2-yl)phenyl]methanol

InChI Identifier

InChI=1S/C10H14O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-6,8,11H,7H2,1-2H3

InChI Key

OIGWAXDAPKFNCQ-UHFFFAOYSA-N

Isomeric SMILES

CC(C)C1=CC=C(CO)C=C1

Average Molecular Weight

150.221

Monoisotopic Molecular Weight

150.104465071

Classification

Description

Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

Monocyclic monoterpenoid
Aromatic monoterpenoid
P-cymene
Phenylpropane
Cumene
Benzyl alcohol
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Aromatic alcohol
Primary alcohol
Organooxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzyl alcohols (CHEBI:27628 )
Cyclic monoterpenes (C06576 )
a small molecule (CPD-1002 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Industrial application:

Food and nutrition:

Flavoring agent

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 79.96%; H 9.39%; O 10.65%	DFC
Melting Point	28 oC
Boiling Point	Bp20 140°	DFC
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	d20 0.98	DFC
Refractive Index	n24D 1.5220	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0550-5900000000-13fde8b7ff0067424578	2015-03-01	View Spectrum
GC-MS	Cuminyl alcohol, non-derivatized, GC-MS Spectrum	splash10-0pvr-3900000000-c32a1e404d8621266f63	Spectrum
GC-MS	Cuminyl alcohol, non-derivatized, GC-MS Spectrum	splash10-0kbr-6900000000-b8aff71f0bcacbaf724d	Spectrum
GC-MS	Cuminyl alcohol, non-derivatized, GC-MS Spectrum	splash10-001i-2900000000-6f5a43e9b74338868204	Spectrum
GC-MS	Cuminyl alcohol, non-derivatized, GC-MS Spectrum	splash10-0pvr-3900000000-c32a1e404d8621266f63	Spectrum
GC-MS	Cuminyl alcohol, non-derivatized, GC-MS Spectrum	splash10-0kbr-6900000000-b8aff71f0bcacbaf724d	Spectrum
GC-MS	Cuminyl alcohol, non-derivatized, GC-MS Spectrum	splash10-001i-2900000000-6f5a43e9b74338868204	Spectrum
Predicted GC-MS	Cuminyl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ap0-2900000000-9ad147d8683aed279c39	Spectrum
Predicted GC-MS	Cuminyl alcohol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ab9-9640000000-185db6c067a7714570b7	Spectrum
Predicted GC-MS	Cuminyl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cuminyl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-001i-0900000000-965c655548a8c5943e62	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-001i-0900000000-d470f06f07de65e5fce2	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-001i-0900000000-51c04eee2d1ab848b219	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-001i-0900000000-66853009b21b51fb3918	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-053r-0900000000-c7fb4e6f07ac2569c2f7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-053r-0900000000-1e3d9dd752086e6d38dc	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0a59-1900000000-13c15749c4bc029cd711	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-0a4i-1900000000-4c8786e398c1c4e67a0f	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-0a4i-2900000000-3b399b4f5dec9e21d1bc	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-066u-4900000000-84309740d600e582f78f	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, positive	splash10-014l-5900000000-1958c690160b7b74935a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, positive	splash10-014l-8900000000-b1d89479c198cc9b0ca6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 12V, positive	splash10-014l-9500000000-db7f4bb92ad19f1a9c58	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-0a4i-1900000000-2d288b863a32ab45d687	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-004i-9000000000-0ae8d2338f48c17984cd	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0a4i-1900000000-be041ab7f72bfcfcad35	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-0a6r-4900000000-24a5e7ac32f1e350402e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-0a6r-7900000000-92fad9231825a0574657	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-056r-9600000000-82ac2a7ea87a2815ed6b	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ue9-0900000000-36f30ea1b9be9f546dd1	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-1900000000-7222268cccd775494a3e	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00lr-3900000000-58cdb5f06cfb7f743bff	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-e8e0e1000bf092241a57	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kb-0900000000-59bdaabd30beafe9a597	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-2900000000-d489f29c4bfd8ceb31c4	2016-08-03	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB31817

CRC / DFC (Dictionary of Food Compounds) ID

DLW56-E:DLW56-E

EAFUS ID

1912

Dr. Duke ID

CUMINYL-ALCOHOL|CUMIN-ALCOHOL|CUMINIC-ALCOHOL

BIGG ID

Not Available

KNApSAcK ID

C00032864

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

536-60-7

GoodScent ID

rw1016451

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

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
wood	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
herb	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
strong	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cumin	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
caraway	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
leather	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.