Milk Composition Database: Showing metabocard for Propionic acid (BMDB0000237)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:27:11 UTC

Update Date

2020-06-04 22:29:10 UTC

MCDB ID

BMDB0000237

Secondary Accession Numbers

BMDB00237

Metabolite Identification

Common Name

Propionic acid

Description

Propionic acid, also known as propionate or acide propanoique, 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. Propionic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Propionic acid exists in all living species, ranging from bacteria to humans. Propionic acid is a potentially toxic compound. Propionic acid has been found to be associated with several diseases known as rheumatoid arthritis, irritable bowel syndrome, colorectal cancer, and ulcerative colitis; also propionic acid has been linked to the inborn metabolic disorders including propionic acidemia.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Acide propanoique	ChEBI
Acide propionique	ChEBI
Carboxyethane	ChEBI
CH3-CH2-COOH	ChEBI
Ethanecarboxylic acid	ChEBI
Ethylformic acid	ChEBI
Metacetonic acid	ChEBI
Methylacetic acid	ChEBI
PA	ChEBI
Propanoic acid	ChEBI
Propioic acid	ChEBI
Propionsaeure	ChEBI
Propoic acid	ChEBI
Pseudoacetic acid	ChEBI
Propionate	Kegg
Ethanecarboxylate	Generator
Ethylformate	Generator
Metacetonate	Generator
Methylacetate	Generator
Propanoate	Generator
Propioate	Generator
Propoate	Generator
Pseudoacetate	Generator
Adofeed	HMDB
Antischim b	HMDB
Luprosil	HMDB
MonoProp	HMDB
Propanate	HMDB
Propcorn	HMDB
Propkorn	HMDB
Prozoin	HMDB
Toxi-check	HMDB
Propionic acid, zinc salt	HMDB
Potassium propionate	HMDB
Chromium propionate	HMDB
Lithium propanoate	HMDB
Zinc propionate	HMDB

Chemical Formula

C₃H₆O₂

Average Molecular Weight

74.0785

Monoisotopic Molecular Weight

74.036779436

IUPAC Name

propanoic acid

Traditional Name

propanoic acid

CAS Registry Number

79-09-4

SMILES

CCC(O)=O

InChI Identifier

InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)

InChI Key

XBDQKXXYIPTUBI-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 acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

saturated fatty acid (CHEBI:30768 )
short-chain fatty acid (CHEBI:30768 )
Straight chain fatty acids (C00163 )
Saturated fatty acids (C00163 )
Straight chain fatty acids (LMFA01010003 )

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-20.7 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000 mg/mL	Not Available
LogP	0.33	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	0.31	ALOGPS
logP	0.48	ChemAxon
logS	0.68	ALOGPS
pKa (Strongest Acidic)	4.75	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	1	ChemAxon
Refractivity	17.27 m³·mol⁻¹	ChemAxon
Polarizability	7.24 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-51f674be972a6c17185b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-691dcd080b30c9898350	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-51f674be972a6c17185b	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9000000000-691dcd080b30c9898350	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00b9-9000000000-abf322c73e6badb078bf	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9100000000-cbfe9e32208652e70047	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-9000000000-1af60fc458a7f351a9b0	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9000000000-aa6e765fc867ac8be641	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-27e0b790e192d1304449	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-004i-9000000000-51f674be972a6c17185b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-004i-9000000000-90d9e0181596093a2f85	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-9000000000-bdd7baa3d1bda886fb77	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00di-9000000000-e73379c8765802cf3228	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00di-9000000000-d6832c04c8b2ca0fdfa3	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-00di-9000000000-d0c93844dbfaed791bb0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-bdd7baa3d1bda886fb77	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-e73379c8765802cf3228	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-d6832c04c8b2ca0fdfa3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-d0c93844dbfaed791bb0	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-47364fadf00a5a2b7e93	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9000000000-76fad523c005a6510264	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9000000000-a1c0234da57ff32c6e12	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-47364fadf00a5a2b7e93	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9000000000-76fad523c005a6510264	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9000000000-a1c0234da57ff32c6e12	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-db59da781a70634d2526	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05fr-9000000000-bea4ff21e6ab6c664412	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-782832f8f5ab85f2ef4f	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-db59da781a70634d2526	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05fr-9000000000-bea4ff21e6ab6c664412	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-782832f8f5ab85f2ef4f	2015-05-27	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00b9-9000000000-0bb3297c4159bed2316e	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected and Quantified	1.9 +/- 0.3 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	3 +/- 1 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	2.3 +/- 0.1 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	2 +/- 1 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	8 +/- 6.92 uM	Free fatty acid	PMID: 29642378	details
Detected and Quantified	4 +/- 2.3 uM	Free fatty acid	PMID: 29642378	details
Detected and Quantified	5.71 +/- 7.02 uM	Free fatty acid	PMID: 29642378	details
Detected and Quantified	0.2 (0.1 - 0.6) uM	Free fatty acid	Harper, W. J., Go...	details
Detected and Quantified	0.2 (0.1 - 0.4) uM	Free fatty acid	Harper, W. J., Go...	details
Detected and Quantified	0.2 (0.1 - 0.5) uM	Free fatty acid	Harper, W. J., Go...	details
Detected and Quantified	0.5 (0.7 - 2.7) uM	Free fatty acid	Harper, W. J., Go...	details
Detected and Quantified	1.0 +/- 0.1 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	2.94 +/- 0.12 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	2.0 +/- 0.1 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	2.0 +/- 0.1 uM	Free fatty acid	PMID: 30994344	details

External Links

HMDB ID

HMDB0000237

DrugBank ID

DB03766

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

30768

References

Synthesis Reference

Zhan, Jianghong; Meng, Wei; Gong, Tao; Huang, Fen-sheng. Preparation of propionic acid by propionaldehyde oxidation. Shihua Jishu Yu Yingyong (2005), 23(6), 421-423.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]
Brigitta Gaspardo, Giuseppe Procida, Saša Volarič, Sandy Sgorlon & Bruno Stefanon (2009). Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009. Italian Journal of Animal Science .
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Showing metabocard for Propionic acid (BMDB0000237)

Structure for BMDB0000237 (Propionic acid)