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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:33:35 UTC

Update Date

2023-02-21 17:26:27 UTC

HMDB ID

HMDB0038275

Secondary Accession Numbers

HMDB38275

Metabolite Identification

Common Name

cis-3-Hexenyl propanoate

Description

cis-3-Hexenyl propanoate is a member of the class of compounds known as carboxylic acid esters. Carboxylic acid esters 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). cis-3-Hexenyl propanoate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). cis-3-Hexenyl propanoate is used as a food additive (EAFUS: Everything Added to Food in the United States). cis-3-Hexenyl propanoate is an apple-, fresh-, and fruity-tasting compound found in fruits, herbs, spices, and tea, which makes cis-3-hexenyl propanoate a potential biomarker for the consumption of these food products. cis-3-Hexenyl propanoate is present in thyme, black tea, and mango and is a flavouring ingredient in baked goods, candies, etc.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

COMPND    HMDB0038275
HETATM    1  C1  UNL     1       4.180   1.105   0.679  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.171   0.839  -0.447  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.000  -0.585  -0.639  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.844  -1.174  -0.491  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.644  -0.453  -0.122  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.438  -0.588  -1.208  1.00  0.00           C  
HETATM    7  O1  UNL     1      -1.611   0.092  -0.903  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.437  -0.098   0.168  1.00  0.00           C  
HETATM    9  O2  UNL     1      -2.123  -0.992   0.997  1.00  0.00           O  
HETATM   10  C8  UNL     1      -3.679   0.675   0.425  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.839  -0.247   0.048  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.068   2.139   1.058  1.00  0.00           H  
HETATM   13  H2  UNL     1       5.187   0.908   0.288  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.975   0.397   1.517  1.00  0.00           H  
HETATM   15  H4  UNL     1       3.723   1.225  -1.366  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.320   1.482  -0.344  1.00  0.00           H  
HETATM   17  H6  UNL     1       3.913  -1.150  -0.922  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.739  -2.267  -0.644  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.186  -1.051   0.737  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.710   0.547   0.268  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.000  -0.123  -2.117  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.595  -1.661  -1.457  1.00  0.00           H  
HETATM   23  H12 UNL     1      -3.774   0.878   1.496  1.00  0.00           H  
HETATM   24  H13 UNL     1      -3.767   1.568  -0.231  1.00  0.00           H  
HETATM   25  H14 UNL     1      -4.490  -1.000  -0.702  1.00  0.00           H  
HETATM   26  H15 UNL     1      -5.666   0.306  -0.411  1.00  0.00           H  
HETATM   27  H16 UNL     1      -5.243  -0.772   0.935  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4    4   17
CONECT    4    5   18
CONECT    5    6   19   20
CONECT    6    7   21   22
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   23   24
CONECT   11   25   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
cis-3-Hexenyl propanoic acid	Generator
(3Z)-3-Hexenyl propionate	HMDB
(Z)-3-Hexen-1-ol, propanoate	HMDB
(Z)-3-Hexenyl propanoate	HMDB
(Z)-3-Hexenyl propionate	HMDB
(Z)-Hex-3-enyl propionate	HMDB
1-Propanoate(3Z)-3-hexen-1-ol	HMDB
3-Hexenyl propionate	HMDB
beta ,Laquo gammaraquo -hexenyl propanoate, cis	HMDB
beta,gamma-Hexenyl propanoate	HMDB
cis-3-Hexenyl N-propionate	HMDB
cis-3-Hexenyl propionate	HMDB
cis-beta -Hexenyl propionate	HMDB
cis-beta-Hexenyl propionate	HMDB
FEMA 3933	HMDB
Is-3-hexenyl N-propionate	HMDB
Propanoate(3Z)-3-hexen-1-ol	HMDB
Propanoate(Z)-3-hexen-1-ol	HMDB
Propanoic acid, (Z)-3-hexenyl ester	HMDB
Propionate(Z)-3-hexen-1-ol	HMDB
Propionic acid cis-3-hexenyl ester	HMDB
(3Z)-Hex-3-en-1-yl propanoic acid	HMDB
Hex-cis-3-enyl propionic acid	Generator

Chemical Formula

C₉H₁₆O₂

Average Molecular Weight

156.2221

Monoisotopic Molecular Weight

156.115029756

IUPAC Name

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

Traditional Name

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

CAS Registry Number

33467-74-2

SMILES

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

InChI Identifier

InChI=1S/C9H16O2/c1-3-5-6-7-8-11-9(10)4-2/h5-6H,3-4,7-8H2,1-2H3/b6-5-

InChI Key

LGTLDEUQCOJGFP-WAYWQWQTSA-N

Chemical Taxonomy

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

Not Available

Ontology

Cellular substructure

Membrane (HMDB: HMDB0038275)

Source

Exogenous

Exogenous (HMDB: HMDB0038275)

Food

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fruit

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	180.00 to 182.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	158.9 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.909 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.74 g/L	ALOGPS
logP	2.74	ALOGPS
logP	2.47	ChemAxon
logS	-2.3	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	6	ChemAxon
Refractivity	46.23 m³·mol⁻¹	ChemAxon
Polarizability	18.5 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.542	31661259
DarkChem	[M-H]-	133.57	31661259
DeepCCS	[M+H]+	136.318	30932474
DeepCCS	[M-H]-	132.56	30932474
DeepCCS	[M-2H]-	169.995	30932474
DeepCCS	[M+Na]+	145.365	30932474
AllCCS	[M+H]+	139.2	32859911
AllCCS	[M+H-H2O]+	135.2	32859911
AllCCS	[M+NH4]+	142.9	32859911
AllCCS	[M+Na]+	143.9	32859911
AllCCS	[M-H]-	140.2	32859911
AllCCS	[M+Na-2H]-	142.2	32859911
AllCCS	[M+HCOO]-	144.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.36 minutes	32390414
Predicted by Siyang on May 30, 2022	14.9215 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.45 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2149.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	442.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	177.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	309.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	207.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	602.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	608.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	78.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1279.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	460.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1303.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	428.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	356.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	419.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	438.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	11.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
cis-3-Hexenyl propanoate	CC\C=C/CCOC(=O)CC	1431.1	Standard polar	33892256
cis-3-Hexenyl propanoate	CC\C=C/CCOC(=O)CC	1063.1	Standard non polar	33892256
cis-3-Hexenyl propanoate	CC\C=C/CCOC(=O)CC	1134.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - cis-3-Hexenyl propanoate EI-B (Non-derivatized)	splash10-0arr-9000000000-113566c588d8678c8221	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - cis-3-Hexenyl propanoate EI-B (Non-derivatized)	splash10-0arr-9000000000-113566c588d8678c8221	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-3-Hexenyl propanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9000000000-875ce5a040a461887480	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-3-Hexenyl propanoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-3-Hexenyl propanoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl propanoate 10V, Positive-QTOF	splash10-0a4i-7900000000-b2a72bdd27c5d789b4e9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl propanoate 20V, Positive-QTOF	splash10-053r-9100000000-24c0e9d6571aa302eb89	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl propanoate 40V, Positive-QTOF	splash10-0a4l-9000000000-5684bf961afaf3ac457e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl propanoate 10V, Negative-QTOF	splash10-0a4i-9700000000-e18c9124e01ba5090dfd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl propanoate 20V, Negative-QTOF	splash10-0ab9-9100000000-74e250270c45971a08a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl propanoate 40V, Negative-QTOF	splash10-0a4i-9000000000-b00d310af5745b23e9d8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl propanoate 10V, Negative-QTOF	splash10-05fs-9200000000-91a7bdf869590a7d328b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl propanoate 20V, Negative-QTOF	splash10-00di-9000000000-204f0f5643623000282a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl propanoate 40V, Negative-QTOF	splash10-0603-9000000000-89352523104172ff3f03	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl propanoate 10V, Positive-QTOF	splash10-0a59-9000000000-e3ae63841aa9c4f57a06	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl propanoate 20V, Positive-QTOF	splash10-0a4i-9000000000-fd1bd0f850efa172a0c2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl propanoate 40V, Positive-QTOF	splash10-0a4i-9000000000-93ec6f12da9729247455	2021-09-23	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB004501

KNApSAcK ID

Not Available

Chemspider ID

4517144

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5365049

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1026871

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for cis-3-Hexenyl propanoate (HMDB0038275)

MOL for HMDB0038275 (cis-3-Hexenyl propanoate)

3D MOL for HMDB0038275 (cis-3-Hexenyl propanoate)

3D SDF for HMDB0038275 (cis-3-Hexenyl propanoate)

3D-SDF for HMDB0038275 (cis-3-Hexenyl propanoate)

PDB for HMDB0038275 (cis-3-Hexenyl propanoate)

3D PDB for HMDB0038275 (cis-3-Hexenyl propanoate)

SMILES for HMDB0038275 (cis-3-Hexenyl propanoate)

INCHI for HMDB0038275 (cis-3-Hexenyl propanoate)

Structure for HMDB0038275 (cis-3-Hexenyl propanoate)

3D Structure for HMDB0038275 (cis-3-Hexenyl propanoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra