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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:16:15 UTC

Update Date

2023-02-21 17:25:15 UTC

HMDB ID

HMDB0036213

Secondary Accession Numbers

HMDB36213

Metabolite Identification

Common Name

cis-3-Hexenyl lactate

Description

cis-3-Hexenyl lactate 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). cis-3-Hexenyl lactate is a sweet, fruity, and green tasting compound. cis-3-Hexenyl lactate has been detected, but not quantified in, alcoholic beverages. This could make cis-3-hexenyl lactate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on cis-3-Hexenyl lactate.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.310   5.954   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.358   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.310   4.414   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.644   3.644   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.644   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.310   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.976   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.025   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.691   2.104   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.025  -0.206   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.691   3.644   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.357   1.334   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    8                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6   12                                                       
CONECT    8    2    9   10                                                  
CONECT    9    8   11   12                                                  
CONECT   10    8                                                            
CONECT   11    9                                                            
CONECT   12    7    9                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

COMPND    HMDB0036213
HETATM    1  C1  UNL     1      -4.442   0.468   0.512  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.553  -0.619  -0.116  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.440  -0.987   0.713  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.178  -0.876   0.380  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.799  -0.342  -0.922  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.057   0.921  -0.805  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.249   0.734  -0.113  1.00  0.00           O  
HETATM    8  C7  UNL     1       2.284  -0.098  -0.418  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.193  -0.805  -1.449  1.00  0.00           O  
HETATM   10  C8  UNL     1       3.474  -0.151   0.457  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.740   0.208  -0.286  1.00  0.00           C  
HETATM   12  O3  UNL     1       3.287   0.736   1.511  1.00  0.00           O  
HETATM   13  H1  UNL     1      -4.735   0.144   1.513  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.962   1.445   0.502  1.00  0.00           H  
HETATM   15  H3  UNL     1      -5.348   0.512  -0.147  1.00  0.00           H  
HETATM   16  H4  UNL     1      -4.253  -1.521  -0.118  1.00  0.00           H  
HETATM   17  H5  UNL     1      -3.428  -0.371  -1.153  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.676  -1.398   1.714  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.373  -1.190   1.095  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.554  -0.176  -1.665  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.099  -1.109  -1.381  1.00  0.00           H  
HETATM   22  H10 UNL     1       0.263   1.332  -1.804  1.00  0.00           H  
HETATM   23  H11 UNL     1      -0.528   1.705  -0.238  1.00  0.00           H  
HETATM   24  H12 UNL     1       3.633  -1.156   0.892  1.00  0.00           H  
HETATM   25  H13 UNL     1       4.581   0.108  -1.386  1.00  0.00           H  
HETATM   26  H14 UNL     1       5.595  -0.409   0.059  1.00  0.00           H  
HETATM   27  H15 UNL     1       4.943   1.284  -0.087  1.00  0.00           H  
HETATM   28  H16 UNL     1       3.072   1.613   1.109  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16   17
CONECT    3    4    4   18
CONECT    4    5   19
CONECT    5    6   20   21
CONECT    6    7   22   23
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   12   24
CONECT   11   25   26   27
CONECT   12   28
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
cis-3-Hexenyl lactic acid	Generator
FEMA 3690	HMDB
(3Z)-Hex-3-en-1-yl 2-hydroxypropanoic acid	Generator

Chemical Formula

C₉H₁₆O₃

Average Molecular Weight

172.2215

Monoisotopic Molecular Weight

172.109944378

IUPAC Name

(3Z)-hex-3-en-1-yl 2-hydroxypropanoate

Traditional Name

(3Z)-hex-3-en-1-yl 2-hydroxypropanoate

CAS Registry Number

61931-81-5

SMILES

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

InChI Identifier

InChI=1S/C9H16O3/c1-3-4-5-6-7-12-9(11)8(2)10/h4-5,8,10H,3,6-7H2,1-2H3/b5-4-

InChI Key

NNLLMULULOBXBY-PLNGDYQASA-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

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0036213)
Cytoplasm (HMDB: HMDB0036213)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036213)

Source

Exogenous

Food

Food (HMDB: HMDB0036213)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0036213)

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0036213)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	71.00 °C. @ 0.70 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	1.575 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.01 g/L	ALOGPS
logP	1.26	ALOGPS
logP	1.53	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	13	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	47.8 m³·mol⁻¹	ChemAxon
Polarizability	19.28 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	141.226	31661259
DarkChem	[M-H]-	137.427	31661259
DeepCCS	[M+H]+	143.385	30932474
DeepCCS	[M-H]-	140.383	30932474
DeepCCS	[M-2H]-	177.152	30932474
DeepCCS	[M+Na]+	152.69	30932474
AllCCS	[M+H]+	142.5	32859911
AllCCS	[M+H-H2O]+	138.7	32859911
AllCCS	[M+NH4]+	146.1	32859911
AllCCS	[M+Na]+	147.1	32859911
AllCCS	[M-H]-	141.8	32859911
AllCCS	[M+Na-2H]-	143.5	32859911
AllCCS	[M+HCOO]-	145.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
cis-3-Hexenyl lactate	CC\C=C/CCOC(=O)C(C)O	1826.8	Standard polar	33892256
cis-3-Hexenyl lactate	CC\C=C/CCOC(=O)C(C)O	1211.2	Standard non polar	33892256
cis-3-Hexenyl lactate	CC\C=C/CCOC(=O)C(C)O	1262.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
cis-3-Hexenyl lactate,1TMS,isomer #1	CC/C=C\CCOC(=O)C(C)O[Si](C)(C)C	1333.7	Semi standard non polar	33892256
cis-3-Hexenyl lactate,1TBDMS,isomer #1	CC/C=C\CCOC(=O)C(C)O[Si](C)(C)C(C)(C)C	1544.2	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 lactate EI-B (Non-derivatized)	splash10-00l5-9000000000-4bdaed6e668e3ddff00c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - cis-3-Hexenyl lactate EI-B (Non-derivatized)	splash10-00l5-9000000000-4bdaed6e668e3ddff00c	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-3-Hexenyl lactate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9000000000-8bf0966397f735d1762d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-3-Hexenyl lactate GC-MS (1 TMS) - 70eV, Positive	splash10-014i-7900000000-9e8079a40d1591dd51f6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-3-Hexenyl lactate 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 lactate 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 lactate 10V, Positive-QTOF	splash10-00di-6900000000-56ad93dc4754dd287ddc	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl lactate 20V, Positive-QTOF	splash10-0089-9200000000-9c472c865bc30131462d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl lactate 40V, Positive-QTOF	splash10-0536-9000000000-8af7d1c27f2398064acc	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl lactate 10V, Negative-QTOF	splash10-00di-9700000000-1cd92a564720c67778c8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl lactate 20V, Negative-QTOF	splash10-00di-9100000000-b00c393ce16ab2ea47d8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl lactate 40V, Negative-QTOF	splash10-00di-9000000000-192c54070582bf745f1d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl lactate 10V, Positive-QTOF	splash10-053s-9000000000-b2185ce51e05011074a0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl lactate 20V, Positive-QTOF	splash10-0a4i-9000000000-690ff2ccdee009a31f5c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl lactate 40V, Positive-QTOF	splash10-0a4i-9000000000-f1a89cd9a17e6fcdd5c5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl lactate 10V, Negative-QTOF	splash10-00di-3900000000-349559f5b3d84be734b5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl lactate 20V, Negative-QTOF	splash10-00dr-9000000000-6d49010335bd639e5351	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl lactate 40V, Negative-QTOF	splash10-00kf-9000000000-0548b8cc13e869ae0a58	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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+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

Cytoplasm
Extracellular

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

FDB015071

KNApSAcK ID

Not Available

Chemspider ID

4516424

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5364231

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1031151

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

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 lactate (HMDB0036213)

MOL for HMDB0036213 (cis-3-Hexenyl lactate)

3D MOL for HMDB0036213 (cis-3-Hexenyl lactate)

3D SDF for HMDB0036213 (cis-3-Hexenyl lactate)

3D-SDF for HMDB0036213 (cis-3-Hexenyl lactate)

PDB for HMDB0036213 (cis-3-Hexenyl lactate)

3D PDB for HMDB0036213 (cis-3-Hexenyl lactate)

SMILES for HMDB0036213 (cis-3-Hexenyl lactate)

INCHI for HMDB0036213 (cis-3-Hexenyl lactate)

Structure for HMDB0036213 (cis-3-Hexenyl lactate)

3D Structure for HMDB0036213 (cis-3-Hexenyl lactate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra