AFCDB: cis-3-Hexenyl acetate (FDB019927)

Record Information

Version

1.0

Creation date

2010-04-08 22:14:41 UTC

Update date

2020-09-17 15:34:24 UTC

Primary ID

FDB019927

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

cis-3-Hexenyl acetate

Description

3-Hexenyl acetate also known as 3-Hexen-1-ol-acetate, belongs to the class of organic compounds known as esters. These are carboxylic acid derivatives in which the acid hydrogen atom has been replaced by an alkyl moiety, forming an ester group. 3-Hexenyl acetate is an acetate ester that results from the formal condensation of acetic acid with (Z)-hex-3-en-1-ol or (E)-hex-3-en-1-ol, for this reason there are two 3-hexenyl-acetate isomers, trans- and cis-hexenyl-acetate. Cis-3-hexenyl acetate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Cis-3-hexenyl acetate is a sweet, apple, and banana tasting compound and it is therefore used as a food additive. Cis-3-hexenyl acetate has been detected, but not quantified in, several different foods such as tamarinds, sunburst squash (pattypan squash), carobs, pepper (C. baccatum), and swedes.

CAS Number

3681-71-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.98 g/L	ALOGPS
logP	2.47	ALOGPS
logP	1.77	ChemAxon
logS	-2.2	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	5	ChemAxon
Refractivity	41.6 m³·mol⁻¹	ChemAxon
Polarizability	16.44 Å³	ChemAxon
Number of Rings	0	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

C8H14O2

IUPAC name

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

InChI Identifier

InChI=1S/C8H14O2/c1-3-4-5-6-7-10-8(2)9/h4-5H,3,6-7H2,1-2H3/b5-4-

InChI Key

NPFVOOAXDOBMCE-PLNGDYQASA-N

Isomeric SMILES

CC\C=C/CCOC(C)=O

Average Molecular Weight

142.1956

Monoisotopic Molecular Weight

142.099379692

Classification

Description

Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Carboxylic acid esters

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

acetate ester (CHEBI:61316 )
Wax monoesters (LMFA07010181 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Animal

Plant:

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 67.57%; H 9.92%; O 22.50%	DFC
Melting Point	Not Available
Boiling Point	Bp12 66°	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)	splash10-00kf-9000000000-b9d062023fc53ab220c0	2015-03-01	View Spectrum
GC-MS	cis-3-Hexenyl acetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-92d448bb2099c2ca8a3e	Spectrum
GC-MS	cis-3-Hexenyl acetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-92d448bb2099c2ca8a3e	Spectrum
Predicted GC-MS	cis-3-Hexenyl acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9000000000-f0acc67e981853b1d215	Spectrum
Predicted GC-MS	cis-3-Hexenyl acetate, 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	splash10-0006-4900000000-5520b4c1a8e0f15f98a3	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9200000000-0c1cce4833b8fb266c60	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-36ca2a715407a2dd7680	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-7900000000-db796ac26e9c69e96528	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4l-9200000000-289d9b380c452347bbc5	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-c8bb62799d02cf5f0d9c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-053r-9000000000-a56ff074a6b1befb6aa1	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-d9067f1965f70e27bba9	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-2a8e4bb754618aaff1ec	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4l-9500000000-24eb76b6258468844355	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-c01bbbf5bed889264ddb	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-1411093172d173726d27	2021-09-25	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 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

HMDB40215

CRC / DFC (Dictionary of Food Compounds) ID

GPT98-M:MGD85-H

EAFUS ID

674

Dr. Duke ID

CIS-3-HEXENYL-ACETATE|CIS-3-HEXEN-1-YL-ACETATE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

3681-71-8

GoodScent ID

rw1001471

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
green	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.
banana	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.
fresh	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruity	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
apple	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.

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).

cis-3-Hexenyl acetate (FDB019927)

Structure for FDB019927 (cis-3-Hexenyl acetate)