AFCDB: p-Mentha-1,3,5,8-tetraene (FDB000812)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:43 UTC

Update date

2020-09-17 15:32:28 UTC

Primary ID

FDB000812

Secondary Accession Numbers

FDB003847
FDB003828
FDB003835

Chemical Information

FooDB Name

p-Mentha-1,3,5,8-tetraene

Description

para-Mentha-1,3,5,8-tetraene, also known as Dehydro-p-cymene, p-alpha-dimethyl-styrene, Habanene or p-Cymenene, belongs to the class of organic compounds known as phenylpropenes. Phenylpropenes are compounds containing a phenylpropene moiety, which consists of a propene substituent bound to a phenyl group. Dehydro-p-cymene is biochemically a monocyclic monoterpenoid as it is synthesized via isoprene units. 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-erythritol-phosphate (MEP) pathway in 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. Dehydro-p-cymene is a hydrophobic, neutral molecule that is insoluble in water. It exists as a clear, colorless oil. Dehydro-p-cymene has a herbaceous, leathery, peppery odor with notes of elemi oil and thyme, as well as a touch of citrus. It has an oregano, clove, basalmic, spicy taste. Dehydro-p-cymene is used as a flavoring agent for Italian dishes and for enhancing habanero spices. Dehydro-p-cymene is found in the highest concentration within star anises but it has also been detected in several different foods, such as lemons, coffee, dill, evergreen blackberries, parsley, citrus, sage, spearmint and pepper.

CAS Number

1195-32-0

Structure

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

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	3.79	ALOGPS
logP	3.52	ChemAxon
logS	-2.9	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	45.07 m³·mol⁻¹	ChemAxon
Polarizability	16.35 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

C10H12

IUPAC name

1-methyl-4-(prop-1-en-2-yl)benzene

InChI Identifier

InChI=1S/C10H12/c1-8(2)10-6-4-9(3)5-7-10/h4-7H,1H2,2-3H3

InChI Key

MMSLOZQEMPDGPI-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

132.2023

Monoisotopic Molecular Weight

132.093900384

Classification

Description

Belongs to the class of organic compounds known as phenylpropenes. Phenylpropenes are compounds containing a phenylpropene moiety, which consists of a propene substituent bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpropenes

Direct Parent

Phenylpropenes

Alternative Parents

Substituents

Phenylpropene
Styrene
Toluene
Aromatic hydrocarbon
Branched unsaturated hydrocarbon
Cyclic olefin
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Biofluid and excreta:

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Cellular process:

Cell signaling

Role

Biological role:

Industrial application:

Food and nutrition:

Flavoring agent

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 90.85%; H 9.15%	DFC
Melting Point	Mp -20°	DFC
Boiling Point	Bp 184-185°	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	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-014i-7900000000-8a35d379c53b742012db	2015-03-01	View Spectrum
Predicted GC-MS	p-Mentha-1,3,5,8-tetraene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-5900000000-42122b872bf255e28667	Spectrum
Predicted GC-MS	p-Mentha-1,3,5,8-tetraene, 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	splash10-001i-0900000000-1a859e9677580ea17b57	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-1900000000-2fd4472dcad1e8a7e949	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0159-7900000000-c9e2399b68bfd80c5f89	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-564cd5c06312dcea67ff	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-abfffa532b094cd93869	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0159-3900000000-f77c6849e823907a8ecf	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-b6dbb79105fa765a1a39	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-e787ac89e5bc523fe920	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-4900000000-f20794dba4e302324ade	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-1900000000-7a77bd4827fc7193683c	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9300000000-8f432d1b83b7ee6d6dc8	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-b7bc284e37a86692377c	2021-09-25	View Spectrum

NMR

Type	Description		View

External Links

ChemSpider ID

56173

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

62385

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB29641

CRC / DFC (Dictionary of Food Compounds) ID

BHZ62-U:BHZ62-U

EAFUS ID

1032

Dr. Duke ID

ALPHA-METHYL-P-METHYL-STYRENE|P-ALPHA-DIMETHYLSTYRENE|ALPHA-DIMETHYLSTYRENE|1-METHYL-4-ISOPROPENYL-BENZENE|4-ISOPROPENYL-TOLUENE

BIGG ID

Not Available

KNApSAcK ID

C00010905

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

1195-32-0

GoodScent ID

rw1018551

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Flavornet: 27576-03-0

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
gasoline	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
citrus	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
pine	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
phenolic	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.
styrene	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
clove	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
guaiacol	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

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).

p-Mentha-1,3,5,8-tetraene (FDB000812)

Structure for FDB000812 (p-Mentha-1,3,5,8-tetraene)