Showing Compound (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one (FDB014294)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:11 UTC

Update date

2019-11-26 03:09:47 UTC

Primary ID

FDB014294

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one

Description

Occurs in peppermint oil, green tea and bergamot oranges (Citrus bergamia) Jasmone is a natural organic compound extracted from the volatile portion of the oil from jasmine flowers. It is a colorless to pale yellow liquid that has the odor of jasmine. Jasmone can exist in two isomeric forms with differing geometry around the pentenyl double bond, cis-jasmone and trans-jasmone. The natural extract contains only the cis form, while synthetic material is often a mixture containing both forms, with the cis form predominating. Both forms have similar odors and chemical properties. (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one is found in many foods, some of which are fig, spearmint, citrus, and sweet orange.

CAS Number

488-10-8

Structure

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

Synonyms

Synonym	Source
cis-Jasmone	Kegg
(Z)-Jasmone	HMDB
2-Cyclopenten-1-one, 3-methyl-2-(2-pentenyl)-, (Z)- (8ci)	HMDB
2-Cyclopenten-1-one, 3-methyl-2-(2Z)-2-pentenyl- (9ci)	HMDB
3-Methyl-2-[(2Z)-2-pentenyl]-2-cyclopenten-1-one	HMDB
cis-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one	HMDB
Jasmone	HMDB
(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one	MeSH
2-Cyclopenten-1-one, 3-methyl-2-(2-pentenyl)-, (Z)- (8CI)	biospider
2-Cyclopenten-1-one, 3-methyl-2-(2Z)-2-pentenyl- (9CI)	biospider
2-cyclopenten-1-one, 3-methyl-2-[(2Z)-2-pentenyl]-	biospider
3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one, (Z)-	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.7 g/L	ALOGPS
logP	3.32	ALOGPS
logP	3.1	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	52.9 m³·mol⁻¹	ChemAxon
Polarizability	19.79 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C11H16O

IUPAC name

3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-one

InChI Identifier

InChI=1S/C11H16O/c1-3-4-5-6-10-9(2)7-8-11(10)12/h4-5H,3,6-8H2,1-2H3/b5-4-

InChI Key

XMLSXPIVAXONDL-PLNGDYQASA-N

Isomeric SMILES

CC\C=C/CC1=C(C)CCC1=O

Average Molecular Weight

164.2441

Monoisotopic Molecular Weight

164.120115134

Classification

Description

belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclic ketones

Alternative Parents

Substituents

Cyclic ketone
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

cyclic ketone (CHEBI:6084 )
Jasmonic acids (C08490 )
Jasmonic acids (LMFA02020009 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 80.44%; H 9.82%; O 9.74%	DFC
Melting Point	Not Available
Boiling Point	Bp12 134-135°	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	n22D 1.4979	DFC

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03dl-9700000000-626f6beb94dae241c8a7	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01r6-9600000000-b7842817d55e1ef34cd5	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03dl-9700000000-626f6beb94dae241c8a7	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01r6-9600000000-b7842817d55e1ef34cd5	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4u-6900000000-4ec9a03205a62c5db571	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-1900000000-b3455ba1815cd60172a3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-066r-7900000000-df4da4ed2a4217531361	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxu-9100000000-1ad974119b61c19d8fcb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-54214296816474e67819	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-9e2bcdc11fb8c55163ab	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9800000000-3aa25aca2cc0986b4e11	JSpectraViewer

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

HMDB35601

CRC / DFC (Dictionary of Food Compounds) ID

JPH11-G:JPJ20-S

EAFUS ID

1955

Dr. Duke ID

JASMONE|CIS-JASMONE

BIGG ID

Not Available

KNApSAcK ID

C00029353

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1016891

SuperScent ID

1549018

Wikipedia ID

Jasmone

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Knapsack: C00001313

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
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti cariogenic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
Insectiphile	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
nematicide	25491	A substance used to destroy pests of the phylum Nematoda (roundworms).	DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
trichomonicide			DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
jasmine	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
woody	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.
floral	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.
jasmin	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
celery	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.