Showing Compound cis-3-Hexenyl hexanoate (FDB011408)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:37 UTC

Update date

2020-09-17 15:31:13 UTC

Primary ID

FDB011408

Secondary Accession Numbers

FDB004497
FDB004498

Chemical Information

FooDB Name

cis-3-Hexenyl hexanoate

Description

cis-3-Hexenyl hexanoate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. cis-3-Hexenyl hexanoate is very hydrophobic, practically insoluble in water, and relatively neutral. cis-3-Hexenyl hexanoate has a fruity, grassy, and green taste. cis-3-Hexenyl hexanoate has been detected in citrus, fruits, herbs and spices, and tea. This could make cis-3-hexenyl hexanoate a potential biomarker for the consumption of these foods. cis-3-Hexenyl hexanoate is the main volatile compound that gives passion fruit its distinctive aroma (https://doi.org/10.1590/S0101-20612011000200023). It is also found in medical plants such as Chamomile (Matricaria recutita L. (https://doi: 10.1021/bk-1993-0525.ch020).

CAS Number

31501-11-8

Structure

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

Synonyms

Synonym	Source
cis-3-Hexenyl hexanoic acid	Generator
(3Z)-3-Hexenyl hexanoate	HMDB
(Z)-3-Hexen-1-ol, hexanoate	HMDB
(Z)-3-Hexenyl hexanoate	HMDB
(Z)-Hex-3-enyl hexanoate	HMDB
3-Hexen-1-ol hexanoate, cis	HMDB
3-Hexenyl ester(Z)-hexanoic acid	HMDB
cis-3-Hexenyl caproate	HMDB
cis-3-Hexenyl caproate (hexanoate)	HMDB
cis-3-Hexenyl hexoate	HMDB
cis-3-Hexenyl N-hexanoate	HMDB
cis-beta -Hexenyl caproate	HMDB
cis-Hexanoic acid, 3-hexenyl ester	HMDB
FEMA 3403	HMDB
Hexanoate(Z)-3-hexen-1-ol	HMDB
Hexanoic acid, (3Z)-3-hexen-1-yl ester	HMDB
Hexanoic acid, (3Z)-3-hexenyl ester	HMDB
Hexanoic acid, 3-hexenyl ester	HMDB
N-Caproic acid cis-3-hexenyl ester	HMDB
(Z)-3-Hexenyl hexanoic acid	Generator
(Z)-3-hexenyl hexanoate	biospider
3-Hexen-1-ol, hexanoate, (Z)-	biospider
3-Hexenyl hexanoate, (Z)-	biospider
3-Hexenyl hexanoate, cis-	biospider
Cis-β-hexenyl caproate	biospider
cis-3-Hexenyl Caproate	biospider
cis-3-Hexenyl hexanoate	db_source
cis-3-Hexenyl Hexoate	biospider
cis-3-Hexenyl n-hexanoate	biospider
cis-Hexanoic Acid, 3-hexenyl ester	biospider
Hexanoic Acid, 3-hexenyl Ester	biospider
Hexanoic acid, 3-hexenyl ester, (Z)-	biospider
n-Caproic acid cis-3-hexenyl ester	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.024 g/L	ALOGPS
logP	4.41	ALOGPS
logP	3.81	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	60.03 m³·mol⁻¹	ChemAxon
Polarizability	24.38 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C12H22O2

IUPAC name

(3Z)-hex-3-en-1-yl hexanoate

InChI Identifier

InChI=1S/C12H22O2/c1-3-5-7-9-11-14-12(13)10-8-6-4-2/h5,7H,3-4,6,8-11H2,1-2H3/b7-5-

InChI Key

RGACQXBDYBCJCY-ALCCZGGFSA-N

Isomeric SMILES

CCCCCC(=O)OCC\C=C/CC

Average Molecular Weight

198.3019

Monoisotopic Molecular Weight

198.161979948

Classification

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Wax monoesters (LMFA07010594 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Biological location:

Biofluid and excreta:

Urine

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 72.68%; H 11.18%; O 16.14%	DFC
Melting Point	Not Available
Boiling Point	Bp12 122°	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
Predicted GC-MS	Hex-cis-3-en-1-ol caproate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001l-9200000000-6b8bf26be0b89f832734	Spectrum
Predicted GC-MS	Hex-cis-3-en-1-ol caproate, 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	splash10-0002-6900000000-60bec3c7e65911e262ea	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001j-9200000000-4188927f3a46e915411f	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0536-9000000000-0e2ff7ec5d5432598d88	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-7900000000-3b843d69c5d696b4a4e6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kb-9800000000-16645f3f41eb56d0cd95	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05mn-9100000000-aee95e7003d3f7477494	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9300000000-16d125a0b88c2beb4311	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9300000000-50a82c936e6d627c174a	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9000000000-15430215c9611d4361e5	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9100000000-7557f7e2d6a690fbe62c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9000000000-7ec4d612cc342b3538a1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a5c-9000000000-079f8ad4c0ad555edbc2	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4509415

ChEMBL ID

CHEMBL3187552

KEGG Compound ID

Not Available

Pubchem Compound ID

5352543

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB33378

CRC / DFC (Dictionary of Food Compounds) ID

GPT98-M:GOD78-X

EAFUS ID

679

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

31501-11-8

GoodScent ID

rw1007981

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

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
fruit	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
prune	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
fruity	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
green	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
waxy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
pear	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
winey	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tropical	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
grassy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
pineapple	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.