Salicylic acid (YMDB01322)

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Identification

YMDB ID

YMDB01322

Name

Salicylic acid

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Salicylic acid, also known as 2-carboxyphenol or 2-hydroxybenzoate, belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids. Salicylic acid exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on Salicylic acid.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

2-Carboxyphenol
2-Hydroxybenzenecarboxylate
2-Hydroxybenzenecarboxylic acid
2-Hydroxybenzoate
2-Hydroxybenzoic acid
Benzoic acid, 2-hydroxy-
Benzoic acid, o-hydroxy-
o-Carboxyphenol
o-Hydroxybenzoate
o-Hydroxybenzoic acid
Orthohydroxybenzoic acid
Phenol-2-carboxylate
Phenol-2-carboxylic acid
Psoriacid-S-Stift
Salicyclic acid
Salicylate
Salicylic acid
Saligel
Salonil
Trans-Ver-Sal
2 Hydroxybenzoic acid
Acid, 2-hydroxybenzoic
Acid, salicylic
Acid, O-hydroxybenzoic
Acid, ortho-hydroxybenzoic
O Hydroxybenzoic acid
Ortho hydroxybenzoic acid
Ortho-hydroxybenzoic acid
Advanced pain relief callus removers
Advanced pain relief corn removers
Clear away wart remover
Compound W
Dr. scholl's callus removers
Dr. scholl's corn removers
Dr. scholl's wart remover kit
Duofil wart remover
Duoplant
Freezone
Ionil
Ionil plus
K 537
K 557
Retarder W
Rutranex
Salicylic acid collodion
Salicylic acid soap
Stri-dex
SA

CAS number

69-72-7

Weight

Average: 138.1207
Monoisotopic: 138.031694058

InChI Key

YGSDEFSMJLZEOE-UHFFFAOYSA-N

InChI

InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)

IUPAC Name

2-hydroxybenzoic acid

Traditional IUPAC Name

salicylic

Chemical Formula

C₇H₆O₃

SMILES

OC(=O)C1=CC=CC=C1O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Salicylic acids

Alternative Parents

Substituents

Salicylic acid
Benzoic acid
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monohydroxybenzoic acid (CHEBI:16914 )

Physical Properties

State

Solid

Charge

Melting point

158 °C

Experimental Properties

Property	Value	Reference
Water Solubility	2.24 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	2.26 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	11.3 g/L	ALOGPS
logP	1.96	ALOGPS
logP	1.98	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	2.79	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.3 m³·mol⁻¹	ChemAxon
Polarizability	12.81 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

extracellular

Organoleptic Properties

Flavour/Odour	Source
Faint	FDB000882
Nutty	FDB000882
Phenolic	FDB000882

SMPDB Pathways

Phenylalanine metabolism

PW002437

KEGG Pathways

Phenylalanine metabolism

ec00360

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-014i-3890000000-62eae168a9d7ab3ada6f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00du-9700000000-e1e2ee6b61d86c596403	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-3890000000-62eae168a9d7ab3ada6f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-2960000000-1b6b46cbb2b643b71448	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0079-8900000000-e8ee46d81fcc1ce3766e	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-006x-8950000000-9ed3a56f2b2654ba281f	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-059j-9600000000-54545731fceee84be340	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-00xu-9500000000-2f1c989b672669aaf083	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0gb9-9000000000-a0049e982e8ecd7ab730	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-0900000000-f1e71df6894bcc8dda74	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-9200000000-f9fd317c182ec7ca90dc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0006-9000000000-2b17aea4ee0ddd6321cf	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-320b7cd879b61439cf42	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-7d1b96d60026076a7ecc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-002b-0496100000-97708001d2a6d031beff	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-002b-0496100000-97708001d2a6d031beff	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-002b-0496100000-97708001d2a6d031beff	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-000i-0900000000-f88c693bac9b89416a52	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-00di-0900000000-2aeace8112266d938c2b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0006-9400000000-b0fb5458dfa73429b976	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0006-9400000000-b0fb5458dfa73429b976	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0006-9100000000-237ee14e8af5262c0dab	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0006-9000000000-3ec5d7a9114e37b8af2a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0006-9000000000-d8fdab29114453b10280	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0006-9000000000-4a337e3639c9f42a9000	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-2900000000-23d1cf43d4dedc979389	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0076-8900000000-f8b39b175209523386d0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-549ee40f4c3d2a965b2d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000l-6900000000-06bd3bf75f92d507fd8d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9100000000-fd107d170618784f2f1f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-3fc7a3b941f5e3e4f7dd	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-00du-9600000000-6d4a0ff2d48d814b5c54	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Okabe, Y., Katayama, N., Iwama, M., Watanabe, H., Ohgi, K., Irie, M., Nitta, K., Kawauchi, H., Takayanagi, Y., Oyama, F., et, a. l. .. (1991). "Comparative base specificity, stability, and lectin activity of two lectins from eggs of Rana catesbeiana and R. japonica and liver ribonuclease from R. catesbeiana." J Biochem 109:786-790.1917903

Synthesis Reference:

Yin, Yingwu; Guo, Qingbin. Preparation of salicylic acid from phenol. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 7pp.

External Links:

Resource	Link
CHEBI ID	16914
HMDB ID	HMDB01895
Pubchem Compound ID	338
Kegg ID	C00805
ChemSpider ID	331
FOODB ID	FDB000882
Wikipedia	Salicylic acid
BioCyc ID	CPD-110

Structure for #<Compound:0xaba719fc>