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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:42:56 UTC

Update Date

2023-02-21 17:20:29 UTC

HMDB ID

HMDB0031403

Secondary Accession Numbers

HMDB31403

Metabolite Identification

Common Name

Cyclohexaneacetic acid

Description

Cyclohexaneacetic acid, also known as cyclohexylethanoic acid, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Cyclohexaneacetic acid is an acetic, caramel, and cheese tasting compound. Based on a literature review a significant number of articles have been published on Cyclohexaneacetic acid.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Cyclohexylethanoic acid	ChEBI
Cyclohexylethanoate	Generator
Cyclohexaneacetate	Generator
Cyclohexaneacetic acid	ChEBI
2-Cyclohexylacetate	Generator, HMDB
Cyclohexane-acetic acid	HMDB
Cyclohexylacetic acid	HMDB
FEMA 2347	HMDB
Hexahydrophenylacetic acid	HMDB
Cyclohexylacetate	Generator

Chemical Formula

C₈H₁₄O₂

Average Molecular Weight

142.1956

Monoisotopic Molecular Weight

142.099379692

IUPAC Name

2-cyclohexylacetic acid

Traditional Name

cyclohexaneacetic acid

CAS Registry Number

5292-21-7

SMILES

OC(=O)CC1CCCCC1

InChI Identifier

InChI=1S/C8H14O2/c9-8(10)6-7-4-2-1-3-5-7/h7H,1-6H2,(H,9,10)

InChI Key

LJOODBDWMQKMFB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acids

Direct Parent

Carboxylic acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:37277 )

Ontology

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0031403)

Exogenous

Food

Food (HMDB: HMDB0031403)

Exogenous (HMDB: HMDB0031403)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0031403)

Role

Biological role

Energy source (HMDB: HMDB0031403)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031403)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031403)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	33 °C	Not Available
Boiling Point	242.00 to 243.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	2.88 mg/mL at 25 °C	Not Available
LogP	2.850	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.97 g/L	ALOGPS
logP	2.53	ALOGPS
logP	2.08	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	4.94	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	38.42 m³·mol⁻¹	ChemAxon
Polarizability	15.95 Å³	ChemAxon
Number of Rings	1	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]+	131.252	31661259
DarkChem	[M-H]-	126.369	31661259
DeepCCS	[M+H]+	138.235	30932474
DeepCCS	[M-H]-	135.674	30932474
DeepCCS	[M-2H]-	171.698	30932474
DeepCCS	[M+Na]+	147.003	30932474
AllCCS	[M+H]+	132.1	32859911
AllCCS	[M+H-H2O]+	127.7	32859911
AllCCS	[M+NH4]+	136.3	32859911
AllCCS	[M+Na]+	137.5	32859911
AllCCS	[M-H]-	133.1	32859911
AllCCS	[M+Na-2H]-	134.9	32859911
AllCCS	[M+HCOO]-	136.9	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.	4.29 minutes	32390414
Predicted by Siyang on May 30, 2022	12.9982 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.83 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	34.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1826.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	401.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	152.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	251.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	336.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	487.3 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	557.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	132.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1089.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	362.9 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	1170.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	362.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	344.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	541.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	358.9 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	140.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyclohexaneacetic acid	OC(=O)CC1CCCCC1	2101.6	Standard polar	33892256
Cyclohexaneacetic acid	OC(=O)CC1CCCCC1	1165.2	Standard non polar	33892256
Cyclohexaneacetic acid	OC(=O)CC1CCCCC1	1241.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cyclohexaneacetic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC1CCCCC1	1291.7	Semi standard non polar	33892256
Cyclohexaneacetic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1CCCCC1	1522.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Cyclohexaneacetic acid EI-B (Non-derivatized)	splash10-03e9-9000000000-b41e00ae96a1ce010432	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Cyclohexaneacetic acid EI-B (Non-derivatized)	splash10-03e9-9000000000-b41e00ae96a1ce010432	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclohexaneacetic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-001m-9200000000-3d8ad65cdc383f430c9d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclohexaneacetic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00gj-9400000000-7cdd05f72c97b91c269c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclohexaneacetic acid 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 - Cyclohexaneacetic acid 10V, Positive-QTOF	splash10-004i-2900000000-b63c5ef41c7cf805c736	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclohexaneacetic acid 20V, Positive-QTOF	splash10-0002-9300000000-1d638fea85a12d8a5e73	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclohexaneacetic acid 40V, Positive-QTOF	splash10-0536-9000000000-2233ab05a2190a337741	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclohexaneacetic acid 10V, Negative-QTOF	splash10-0007-4900000000-f7f783e99f31ea43521f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclohexaneacetic acid 20V, Negative-QTOF	splash10-006w-7900000000-204d44166f324eeec4ec	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclohexaneacetic acid 40V, Negative-QTOF	splash10-052g-9100000000-9c2931c97170ee18763e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclohexaneacetic acid 10V, Positive-QTOF	splash10-003r-9500000000-7adc865363cd35cd86cf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclohexaneacetic acid 20V, Positive-QTOF	splash10-0564-9100000000-7601578deffb68f98914	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclohexaneacetic acid 40V, Positive-QTOF	splash10-0a5a-9000000000-ad139cf8b04b6b2540a8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclohexaneacetic acid 10V, Negative-QTOF	splash10-0006-1900000000-ba39166ce90fde52906a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclohexaneacetic acid 20V, Negative-QTOF	splash10-0006-9700000000-52ea16a38cf8013a8c46	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclohexaneacetic acid 40V, Negative-QTOF	splash10-052f-9200000000-2590b1d09f1ca638d6ed	2021-09-22	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
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

FDB003477

KNApSAcK ID

Not Available

Chemspider ID

20080

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21363

PDB ID

Not Available

ChEBI ID

37277

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1028891

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Iwaki H, Nakai E, Nakamura S, Hasegawa Y: Isolation and characterization of new cyclohexylacetic acid-degrading bacteria. Curr Microbiol. 2008 Aug;57(2):107-10. doi: 10.1007/s00284-008-9158-0. Epub 2008 Apr 8. [PubMed:18392890 ]
Quesnel DM, Bhaskar IM, Gieg LM, Chua G: Naphthenic acid biodegradation by the unicellular alga Dunaliella tertiolecta. Chemosphere. 2011 Jul;84(4):504-11. doi: 10.1016/j.chemosphere.2011.03.012. Epub 2011 Apr 2. [PubMed:21459409 ]
Valente MM, Bortolotto V, Cuccurazzu B, Ubezio F, Meneghini V, Francese MT, Canonico PL, Grilli M: alpha2delta ligands act as positive modulators of adult hippocampal neurogenesis and prevent depression-like behavior induced by chronic restraint stress. Mol Pharmacol. 2012 Aug;82(2):271-80. doi: 10.1124/mol.112.077636. Epub 2012 May 9. [PubMed:22572885 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Cyclohexaneacetic acid (HMDB0031403)

MOL for HMDB0031403 (Cyclohexaneacetic acid)

3D MOL for HMDB0031403 (Cyclohexaneacetic acid)

3D SDF for HMDB0031403 (Cyclohexaneacetic acid)

3D-SDF for HMDB0031403 (Cyclohexaneacetic acid)

PDB for HMDB0031403 (Cyclohexaneacetic acid)

3D PDB for HMDB0031403 (Cyclohexaneacetic acid)

SMILES for HMDB0031403 (Cyclohexaneacetic acid)

INCHI for HMDB0031403 (Cyclohexaneacetic acid)

Structure for HMDB0031403 (Cyclohexaneacetic acid)

3D Structure for HMDB0031403 (Cyclohexaneacetic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra