Salicylic acid

Modify Date: 2024-01-02 15:15:03

Salicylic acid Structure
Salicylic acid structure
 Common Name Salicylic acid
CAS Number 69-72-7 Molecular Weight 138.121
Density 1.44 Boiling Point 211 ºC (20 mmHg)
Molecular Formula C7H6O3 Melting Point 158-161 °C(lit.)
MSDS Chinese USA Flash Point 157 ºC
Symbol GHS05 GHS07
GHS05, GHS07		 Signal Word Danger

 Use of Salicylic acid


Salicylic acid inhibits cyclo-oxygenase-2 (COX-2) activity independently of transcription factor (NF-κB) activation.

 Names

Name salicylic acid
Synonym More Synonyms

 Salicylic acid Biological Activity

Description Salicylic acid inhibits cyclo-oxygenase-2 (COX-2) activity independently of transcription factor (NF-κB) activation.
Related Catalog
Target

COX-2

Autophagy

Mitophagy

In Vitro Salicylic acid is an effective inhibitor of COX-2 activity at concentrations far below those required to inhibit NF-κB (20 mg/mL) activation. Salicylic acid inhibits prostaglandin E2 release when add together with interleukin 1β for 24 hr with an IC50 value of 5 μg/mL, an effect that is independent of NF-κB activation or COX-2 transcription or translation. Salicylic acid acutely (30 min) also causes a concentration-dependent inhibition of COX-2 activity measured in the presence of 0, 1, or 10 μM exogenous arachidonic acid. In contrast, when exogenous arachidonic acid is increased to 30 μM, Salicylic acid is a very weak inhibitor of COX-2 activity with an IC50 of >100 μg/mL. When added together with IL-1β for 24 hr, Salicylic acid causes a concentration-dependent inhibition of PGE2 release with an apparent IC50 value of approximately 5 μg/mL. The ability of Salicylic acid to directly inhibit COX-2 activity in A549 cells is tested after a 30-min exposure period, followed by the addition of different concentrations of exogenous arachidonic acid (1, 10, and 30 μM). Salicylic acid causes a concentration-dependent inhibition of COX-2 activity in the absence of added arachidonic acid or in the presence of 1 or 10 μM exogenous substrate with an apparent IC50 value of approximately 5 μg/mL. However, when the same experiments are performed using 30 μM arachidonic acid, Salicylic acid is an ineffective inhibitor of COX-2 activity, with an apparent IC50 value of more than 100 μg/mL, and achieves a maximal inhibition of less than 50%[1].
In Vivo In C57Bl/6 DIO mice, Salicylic acid decreases both fasting and postprandial plasma glucose levels. Furthermore, there is a trend to reduce plasma triglyceride levels after Salicylic acid treatment in C57Bl/6 DIO mice (P=0.059). Salicylic acid significantly reduces 11β-HSD1 mRNA in omental adipose tissue in C57Bl/6 DIO mice, with a similar trend in mesenteric adipose (P=0.057). In mesenteric adipose of C57Bl/6 DIO mice, Salicylic acid also reduces 11β-HSD1 enzyme activity[2].
Kinase Assay Human purified COX-2 are and the cofactors Glutathione (5 mM), Adrenaline (5 mM), and Hematin (1 μM) are dissolved in 50 mM Tris buffer (pH 7.5). Hematin is first dissolved in a concentrated stock of 100 mM in 1 M NaOH before being further diluted in Tris buffer. Enzyme reactions are carried out in individual wells of 96-well plates with a final reaction volume of 200 μL. Different concentrations of Salicylic acid are added to the plate, followed by the addition of 10 units of enzyme (180 μL). The plates are incubated at 37° for 30 min before Arachidonic acid (10 nM to 30 μM) is added for a further 15 min. The reaction is stopped by heating the plate to 100°C for 5 min. The 96-well plate is then centrifuged at 10,000× g for 10 min, and appropriated samples are removed and added into the radioimmunoassay[1].
Cell Assay To assess the direct effect of Salicylic acid on COX-2 activity after induction has occurred, A549 cells are first treated with IL-1β for 24 hr, and the culture medium is replaced with DMEM containing different concentrations of Salicylic acid(10, 100 and 1000 μg/mL). Cells are incubated at 37°C for 30 min. Arachidonic acid (1-30 μM) is then added for 15 min, and the medium is removed for the measurement of PGE2[1].
Animal Admin Mice[2] Adult male C57Bl/6 mice are at age 12 weeks. Diet-induced obese C57Bl/6 mice (C57Bl/6 DIO) are given 10 weeks of high-fat diet (58% fat, 12% sucrose) before treatment. Salicylic acid (120 mg/kg/day) is administered from 1 week after arriving (C57Bl/6 Lean), after 10 weeks of high-fat feeding (C57Bl/6 DIO), or after achieving target weight (HSD1KO-DIO) for 4 weeks to groups of n=8 via osmotic minipumps implant subcutaneously between the scapulae.
References

[1]. Mitchell JA, et al. Sodium salicylate inhibits cyclo-oxygenase-2 activity independently of transcription factor (nuclear factor kappaB) activation: role of arachidonic acid. Mol Pharmacol. 1997 Jun;51(6):907-12.

[2]. Nixon M, et al. Salicylate downregulates 11β-HSD1 expression in adipose tissue in obese mice and in humans, mediating insulin sensitization. Diabetes. 2012 Apr;61(4):790-6.

 Chemical & Physical Properties

Density 1.44
Boiling Point 211 ºC (20 mmHg)
Melting Point 158-161 °C(lit.)
Molecular Formula C7H6O3
Molecular Weight 138.121
Flash Point 157 ºC
Exact Mass 138.031693
PSA 57.53000
LogP 2.06
Vapour density 4.8 (vs air)
Vapour Pressure 0.0±0.7 mmHg at 25°C
Index of Refraction 1.616
Storage condition Store at RT.
Water Solubility 1.8 g/L (20 ºC)

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
VO0525000
CHEMICAL NAME :
Salicylic acid
CAS REGISTRY NUMBER :
69-72-7
BEILSTEIN REFERENCE NO. :
0774890
LAST UPDATED :
199710
DATA ITEMS CITED :
38
MOLECULAR FORMULA :
C7-H6-O3
MOLECULAR WEIGHT :
138.13
WISWESSER LINE NOTATION :
QVR BQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration into the eye
SPECIES OBSERVED :
Rodent - rabbit
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
57 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Ear) - tinnitus
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
111 mg/kg/10D-I
TOXIC EFFECTS :
Sense Organs and Special Senses (Ear) - change in acuity Cardiac - pulse rate increase, without fall in BP Nutritional and Gross Metabolic - body temperature increase
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
891 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - muscle weakness
TYPE OF TEST :
LC50 - Lethal concentration, 50 percent kill
ROUTE OF EXPOSURE :
Inhalation
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>900 mg/m3/1H
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Liver - other changes Skin and Appendages - hair
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
157 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - tremor Nutritional and Gross Metabolic - body temperature decrease
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
480 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
300 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression
TYPE OF TEST :
LD60 - Lethal Dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
520 mg/kg
TOXIC EFFECTS :
Cardiac - change in rate Behavioral - muscle weakness
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
184 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
400 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
1300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
6 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LC50 - Lethal concentration, 50 percent kill
ROUTE OF EXPOSURE :
Inhalation
SPECIES OBSERVED :
Mammal - species unspecified
DOSE/DURATION :
>300 mg/m3
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
40 mg/kg
SEX/DURATION :
female 20-21 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - parturition
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1050 mg/kg
SEX/DURATION :
female 8-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1050 mg/kg
SEX/DURATION :
female 8-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
700 mg/kg
SEX/DURATION :
female 8-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
350 mg/kg
SEX/DURATION :
female 8-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
380 mg/kg
SEX/DURATION :
female 9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1 gm/kg
SEX/DURATION :
female 17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
500 mg/kg
SEX/DURATION :
female 9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
100 mg/kg
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 46,305,1977 *** REVIEWS *** TOXICOLOGY REVIEW AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 34,173,1928 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 67680 No. of Facilities: 6955 (estimated) No. of Industries: 39 No. of Occupations: 57 No. of Employees: 61410 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 67680 No. of Facilities: 2133 (estimated) No. of Industries: 40 No. of Occupations: 50 No. of Employees: 51922 (estimated) No. of Female Employees: 20096 (estimated)

 Safety Information

Symbol GHS05 GHS07
GHS05, GHS07
Signal Word Danger
Hazard Statements H302-H318
Precautionary Statements P280-P301 + P312 + P330-P305 + P351 + P338 + P310
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn:Harmful
Risk Phrases R22;R36/37/38;R41
Safety Phrases S26-S39-S37/39
RIDADR 1993.0
WGK Germany 1
RTECS VO0525000
Hazard Class 3.0
HS Code 2918211000

 Synthetic Route

 Customs

HS Code 2918211000
Summary 2918211000. VAT:17.0%. Tax rebate rate:9.0%. . MFN tariff:6.5%. General tariff:20.0%

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 Synonyms

Verrugon
Acid, Salicylic
Duoplant
Freezone
MFCD00002439
Acid, o-Hydroxybenzoic
SAX
EINECS 200-712-3
Saligel
Hydroxybenzenecarboxylic acid
Salonil
phenol-carboxylic acid
Stri-Dex
Benzoic acid, 2-hydroxy-
ORTHO-HYDROXYBENZOIC ACID
2-Hydroxybenzenecarboxylic acid
2 Hydroxybenzoic Acid
Salicylic acid
Acid, 2-Hydroxybenzoic
Benzoic acid, o-hydroxy-
2-hydroxy-benzoic acid
ortho Hydroxybenzoic Acid
Ionil
2-hydroxybenzoic acid
Acid, ortho-Hydroxybenzoic
o-hydroxybenzoic acid
Duofilm
Rutranex
Keralyt
Lamivudine Impurity 3
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