SALICYLIC ACID
Relevant Data
Food Additives Approved in the United States
Flavouring Substances Approved by European Union:
General Information
| Chemical Names: | o-HYDROXYBENZOIC ACID; o-OXYBENZOIC ACID |
| CAS number: | 69-72-7 |
| JECFA number: | 958 |
| FEMA number: | 3985 |
| Functional Class: |
Food Additives PRESERVATIVE |
From apps.who.int
Evaluations
| Evaluation year: | 1961 |
| ADI: | NO ADI ALLOCATED |
| Meeting: | 06 |
| Specs Code: | O |
| Comments: | Unsuitable as a food additive |
| Report: | NMRS 31/TRS 228-JECFA 6/86 |
| Tox Monograph: | NMRS 31/TRS 228-JECFA 6/87 |
| Specification: | NOT PREPARED |
From apps.who.int
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 338 |
| IUPAC Name | 2-hydroxybenzoic acid |
| InChI | InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10) |
| InChI Key | YGSDEFSMJLZEOE-UHFFFAOYSA-N |
| Canonical SMILES | C1=CC=C(C(=C1)C(=O)O)O |
| Molecular Formula | C7H6O3 |
| Wikipedia | salicylate |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 138.122 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 1 |
| Complexity | 133.0 |
| CACTVS Substructure Key Fingerprint | A A A D c Y B g M A A A A A A A A A A A A A A A A A A A A A A A A A A w A A A A A A A A A A A B A A A A G g A A C A A A D A S A m A A w D o A A A g C I A i D S C A A C A A A k I A A I i A E G C M g I J z a C F R K A c U A l 4 B E I m Y e I y C C O A A A A A A A I A A A A A A A A A B A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 57.5 |
| Monoisotopic Mass | 138.032 |
| Exact Mass | 138.032 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 10 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.6165 |
| Human Intestinal Absorption | HIA+ | 0.9756 |
| Caco-2 Permeability | Caco2+ | 0.8867 |
| P-glycoprotein Substrate | Non-substrate | 0.7340 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9815 |
| Non-inhibitor | 0.9937 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9167 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8764 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7962 |
| CYP450 2D6 Substrate | Non-substrate | 0.9233 |
| CYP450 3A4 Substrate | Non-substrate | 0.7660 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9517 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7984 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9659 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7644 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8675 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8525 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9631 |
| Non-inhibitor | 0.9734 | |
| AMES Toxicity | Non AMES toxic | 0.9829 |
| Carcinogens | Non-carcinogens | 0.8627 |
| Fish Toxicity | High FHMT | 0.7460 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.7307 |
| Honey Bee Toxicity | High HBT | 0.7317 |
| Biodegradation | Ready biodegradable | 0.8086 |
| Acute Oral Toxicity | III | 0.7939 |
| Carcinogenicity (Three-class) | Non-required | 0.7871 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.6128 | LogS |
| Caco-2 Permeability | 1.0291 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.2160 | LD50, mol/kg |
| Fish Toxicity | 1.9177 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.3852 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | None |
|---|---|
| Mechanism of Toxicity | Salicylic acid directly and irreversibly inhibits the activity of both types of cyclo-oxygenases (COX-1 and COX-2) to decrease the formation of precursors of prostaglandins and thromboxanes from arachidonic acid. Salicylate may competitively inhibit prostaglandin formation. Salicylate's antirheumatic (nonsteroidal anti-inflammatory) actions are a result of its analgesic and anti-inflammatory mechanisms. Salicylic acid is a key ingredient in many skin-care products for the treatment of acne, psoriasis, calluses, corns, keratosis pilaris, and warts. It works by causing the cells of the epidermis to slough off more readily, preventing pores from clogging up, and allowing room for new cell growth. Because of its effect on skin cells, salicylic acid is used in several shampoos used to treat dandruff. Salicylic acid is also used as an active ingredient in gels which remove verrucas (plantar warts). Salicylic acid inhibits the oxidation of uridine-5-diphosphoglucose (UDPG) competitively with nicotinamide adenosine dinucleotide (NAD) and noncompetitively with UDPG. It also competitively inhibits the transferring of glucuronyl group of uridine-5-phosphoglucuronic acid (UDPGA) to the phenolic acceptor. The wound-healing retardation action of salicylates is probably due mainly to its inhibitory action on mucopolysaccharide synthesis. |
| Metabolism | None |
| Toxicity Values | Oral rat LD50: 891 mg/kg. Inhalation rat LC50: > 900 mg/m3/1hr. Irritation: skin rabbit: 500 mg/24H mild. Eye rabbit: 100 mg severe. |
| Lethal Dose | None |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | None |
| Health Effects | Investigated as a mutagen and reproductive effector. |
| Treatment | None |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Benzoic acids and derivatives |
| Intermediate Tree Nodes | Hydroxybenzoic acid derivatives - Salicylic acid and derivatives |
| Direct Parent | Salicylic acids |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| 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 |
| Description | This compound belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids. |
From ClassyFire
Targets
- General Function:
- Prostaglandin-endoperoxide synthase activity
- Specific Function:
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the generation of thromboxane A2 (TXA2), which promotes platelet activation and aggregation, vasoconstriction and proliferation of vascular smooth muscle cells.
- Gene Name:
- PTGS1
- Uniprot ID:
- P23219
- Molecular Weight:
- 68685.82 Da
References
- Vane JR: Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat New Biol. 1971 Jun 23;231(25):232-5. [5284360 ]
- General Function:
- Prostaglandin-endoperoxide synthase activity
- Specific Function:
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, phenotypic changes, resistance to apoptosis and tumor angiogenesis. In cancer cells, PTGS2 is a key step in the production of prostaglandin E2 (PGE2), which plays important roles in modulating motility, proliferation and resistance to apoptosis.
- Gene Name:
- PTGS2
- Uniprot ID:
- P35354
- Molecular Weight:
- 68995.625 Da
References
- Elvira C, Gallardo A, Lacroix N, Schacht E, San Roman J: Incorporation of salicylic acid derivatives to hydrophilic copolymer systems with biomedical applications. J Mater Sci Mater Med. 2001 Jun;12(6):535-42. [15348270 ]
- General Function:
- Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
- Specific Function:
- Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
- Gene Name:
- AKR1C1
- Uniprot ID:
- Q04828
- Molecular Weight:
- 36788.02 Da
References
- Dhagat U, Carbone V, Chung RP, Matsunaga T, Endo S, Hara A, El-Kabbani O: A salicylic acid-based analogue discovered from virtual screening as a potent inhibitor of human 20alpha-hydroxysteroid dehydrogenase. Med Chem. 2007 Nov;3(6):546-50. [18045204 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
- Gene Name:
- AR
- Uniprot ID:
- P10275
- Molecular Weight:
- 98987.9 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
From T3DB