AFCDB: Acetic acid (FDB008299)

Record Information

Version

1.0

Creation date

2010-04-08 22:08:01 UTC

Update date

2020-04-21 18:03:32 UTC

Primary ID

FDB008299

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Acetic acid

Description

Has been used as a food preservative since antiquity. It is used in - and contributes to - the flavour of pickles, sauces, mayonnaise and salad dressings. Acts synergistically with lactic and sorbic acid, and is more effective against yeasts and bacteria than against moulds. It is used in food processing as a flavour enhancer, flavouring agent, pH control agent, pickling agent, solvent and formulation aid Acetic acid is an organic compound with the chemical formula CH3COOH. It is a colourless liquid that when undiluted is also called glacial acetic acid. As the main component of vinegar, it has a distinctive sour taste and pungent smell. Acetic acid is found in many foods, some of which are garden rhubarb, wild celery, pear, and ginger.

CAS Number

64-19-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	323 g/L	ALOGPS
logP	-0.12	ALOGPS
logP	-0.22	ChemAxon
logS	0.73	ALOGPS
pKa (Strongest Acidic)	4.54	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	0	ChemAxon
Refractivity	12.64 m³·mol⁻¹	ChemAxon
Polarizability	5.34 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

C2H4O2

IUPAC name

acetic acid

InChI Identifier

InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)

InChI Key

QTBSBXVTEAMEQO-UHFFFAOYSA-N

Isomeric SMILES

CC(O)=O

Average Molecular Weight

60.052

Monoisotopic Molecular Weight

60.021129372

Classification

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

monocarboxylic acid (CHEBI:15366 )
Straight chain fatty acids (C00033 )
Saturated fatty acids (C00033 )
Straight chain fatty acids (LMFA01010002 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 40.00%; H 6.71%; O 53.28%	DFC
Melting Point	Mp 16.7°	DFC
Boiling Point	Bp 118°	DFC
Experimental Water Solubility	1000 mg/mL at 25 oC	MERCK INDEX (1996)
Experimental logP	-0.17	HANSCH,C ET AL. (1995)
Experimental pKa	pKa 4.78 (25°)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d204 1.05	DFC
Refractive Index	n25D 1.3696	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-01oy-9000000000-181ada67a3e5798d4419	2014-09-20	View Spectrum
GC-MS	Acetic acid, non-derivatized, GC-MS Spectrum	splash10-0007-9000000000-a9a21f72ec25efbc1650	Spectrum
GC-MS	Acetic acid, non-derivatized, GC-MS Spectrum	splash10-0007-9000000000-a9a21f72ec25efbc1650	Spectrum
Predicted GC-MS	Acetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03dl-9000000000-b96ad978047d68715939	Spectrum
Predicted GC-MS	Acetic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00du-9100000000-8154631f77f485ee31b9	Spectrum
Predicted GC-MS	Acetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acetic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-9000000000-044b361cb9f5775c43fe	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-01ox-9000000000-6437eb5f6a38c054dc37	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-0505dfa8ee07a18a3ef3	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0007-9000000000-a0d65dd4e056c1482aaa	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0a4i-9000000000-a845ea0157abb3d7783b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4i-9000000000-42ec023f024176a1c692	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-9000000000-2bbab52cd9d076b89b2c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-9000000000-fb6d2f6298dd5bc37c2e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9000000000-bc47c47ade16451259c7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-a845ea0157abb3d7783b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-42ec023f024176a1c692	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-2bbab52cd9d076b89b2c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-fb6d2f6298dd5bc37c2e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-bc47c47ade16451259c7	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9000000000-528a9b0672006e635695	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9000000000-a784dfc5bd03549bc072	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ox-9000000000-b71ac391a2b191d6ef01	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-034375837c4c93ddf819	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-f031d1f9ac695f944bbd	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-64f8448a12a6d78d84e4	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-c01bbbf5bed889264ddb	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-c01bbbf5bed889264ddb	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-91545f233d6bc755c516	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-ee98b120aa7fd044da72	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-87bbaed151efac084591	2021-09-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	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)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

15366

Phenol-Explorer ID

Not Available

DrugBank ID

DB03166

HMDB ID

HMDB00042

CRC / DFC (Dictionary of Food Compounds) ID

DFR91-W:DFR91-W

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

64-19-7

GoodScent ID

rw1097191

SuperScent ID

Not Available

Wikipedia ID

Acetic_acid

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

Descriptor	ID	Definition	Reference
acidulant	64047	Any substance which is added to food to preserve or enhance its flavour and/or appearance.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti otitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti salmonella	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti vaginitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
expectorant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
keratitigenic			DUKE
mucolytic	77034	A compound that alters the structure of mucus so as to decrease its viscosity and thereby facilitate its removal by ciliary action and expectoration. Compare with antitussives, which suppress the cough reflex, and expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing.	DUKE
osteolytic			DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
protisticide			DUKE
spermicide			DUKE
ulcerogenic			DUKE
verrucolytic			DUKE

Enzymes

Name	Gene Name	UniProt ID
Liver carboxylesterase 1	CES1	P23141
Acetylcholinesterase	ACHE	P22303
Serum paraoxonase/lactonase 3	PON3	Q15166
Serum paraoxonase/arylesterase 1	PON1	P27169
Serum paraoxonase/arylesterase 2	PON2	Q15165
60 kDa lysophospholipase	ASPG	Q86U10
Sialate O-acetylesterase	SIAE	Q9HAT2
S-formylglutathione hydrolase	ESD	P10768
Cocaine esterase	CES2	O00748
Acylphosphatase-2	ACYP2	P14621
Acylphosphatase-1	ACYP1	P07311
Aspartoacylase	ASPA	P45381
Aspartoacylase-2	ACY3	Q96HD9
N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase	PIGL	Q9Y2B2
Acetyl-coenzyme A synthetase, cytoplasmic	ACSS2	Q9NR19
Acetyl-coenzyme A synthetase 2-like, mitochondrial	ACSS1	Q9NUB1
Hydroxymethylglutaryl-CoA lyase, mitochondrial	HMGCL	P35914
Acyl-coenzyme A thioesterase 12	ACOT12	Q8WYK0
Platelet-activating factor acetylhydrolase	PLA2G7	Q13093
Platelet-activating factor acetylhydrolase IB subunit gamma	PAFAH1B3	Q15102
Platelet-activating factor acetylhydrolase IB subunit beta	PAFAH1B2	P68402
Platelet-activating factor acetylhydrolase 2, cytoplasmic	PAFAH2	Q99487
Putative N-acetylglucosamine-6-phosphate deacetylase	AMDHD2	Q9Y303

Pathways

Name	SMPDB Link	KEGG Link
Amino Sugar Metabolism	SMP00045	map00520
Ethanol Degradation	SMP00449	Not Available
Fatty Acid Biosynthesis	SMP00456	Not Available
Pyruvate Metabolism	SMP00060	map00620

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
sour	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.
sharp	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
pungent	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
vinegar	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Acetic acid (FDB008299)

Structure for FDB008299 (Acetic acid)