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| CAS No.: | 119-36-8 |
|---|---|
| Name: | Methyl salicylate |
| Article Data: | 265 |
| Cas Database | |
| Molecular Structure: | |
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| Formula: | C8H8O3 |
| Molecular Weight: | 152.15 |
| Synonyms: | Gaultheria Oil, artificial;Benzoic acid,2-hydroxy-,esters,methyl ester;Teaberry oil;Gaultheriaoel;2-(Methoxycarbonyl)phenol;Wintergruenoel;o-Hydroxybenzoic acid, methyl ester;Natural Wintergreen Oil;Betula;Salicylic acid, methyl ester;Methyl salicylate (JP14/NF);Oil of Wintergreen;Methyl salicylate BP;Methyl Hydroxy benzoate;Methyl salicylic acid;methyl salicylate;2-carbomethoxyphenol; methyl o-hydroxybenzoate;Wintergreen oil;Methyl 2-hydroxybenzoate;Gaultheria oil;Metylester kyseliny salicylove;Methyl o-hydroxybenzoate;Benzoic acid, 2-hydroxy-, methyl ester;Spicewood Oil;Flucarmit; |
| EINECS: | 204-317-7 |
| Density: | 1.209 g/cm3 |
| Melting Point: | -8 °C |
| Boiling Point: | 222 °C at 760 mmHg |
| Flash Point: | 86.8 °C |
| Solubility: | 0.07 g/100 mL (20 °C) in water |
| Appearance: | colourless liquid with an odour of wintergreen |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 22-36/38-36/37/38 |
| Safety: | 26-36-24/25 |
| Transport Information: | N/A |
| PSA: | 46.53000 |
| LogP: | 1.17880 |
1-carbomethoxybenzene 1,2-oxide
methyl salicylate
| Conditions | Yield |
|---|---|
| With trifluoroacetic acid In tetrahydrofuran; water pH 0.1; further pH; | 100% |
| With phosphate buffer In tetrahydrofuran; water Product distribution; Mechanism; other pH; | 100% |
2-trimethylsilanyloxy-benzoic acid methyl ester
methyl salicylate
| Conditions | Yield |
|---|---|
| montmorillonite K-10 for 0.05h; Solid phase reaction; desilylation; microwave irradiation; | 100% |
| With dichloro bis(acetonitrile) palladium(II) In water; acetone at 75℃; for 14h; | 93% |
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1. Introduction of Methyl salicylate
Methyl salicylate is colorless or light pale yellow liquid with Characteristic odor. The IUPAC Name of it is methyl 2-hydroxybenzoate.
2. Properties of Methyl salicylate
Index of Refraction: 1.547
Molar Refractivity: 39.9 cm3
Molar Volume: 125.7 cm3
Polarizability: 15.82×10-24cm3
Surface Tension: 45.7 dyne/cm
Density: 1.209 g/cm3
Flash Point: 86.8 °C
Enthalpy of Vaporization: 47.71 kJ/mol
Melting Point: -8 °C
Boiling Point: 222 °C at 760 mmHg
Vapour Pressure: 0.07 mmHg at 25°C
Water Solubility: 0.07 g/100 mL (20 ºC)
Stability: Stable. Incompatible with strong oxidizing agents, strong bases.
3. Structure Descriptors of Methyl salicylate
Product Categories: INORGANIC & ORGANIC CHEMICALS;FINE Chemical & INTERMEDIATES;Cosmetic Ingredients & Chemicals
Canonical SMILES: COC(=O)C1=CC=CC=C1O
InChI: InChI=1S/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3
InChIKey: OSWPMRLSEDHDFF-UHFFFAOYSA-N
4. Toxicity of Methyl salicylate
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| child | LDLo | oral | 228mg/kg (228mg/kg) | LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: NAUSEA OR VOMITING | American Journal of Diseases of Children. Vol. 69, Pg. 37, 1945. |
| child | LDLo | oral | 700mg/kg (700mg/kg) | PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: GENERAL ANESTHETIC | Archives of Disease in Childhood. Vol. 28, Pg. 475, 1953. |
| dog | LD50 | oral | 2100mg/kg (2100mg/kg) | LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES GASTROINTESTINAL: NAUSEA OR VOMITING GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Food and Cosmetics Toxicology. Vol. 16, Pg. 821, 1978. |
| dog | LDLo | subcutaneous | 2250mg/kg (2250mg/kg) | Food and Cosmetics Toxicology. Vol. 16, Pg. 821, 1978. | |
| guinea pig | LD50 | oral | 700mg/kg (700mg/kg) | "Industrial Hygiene and Toxicology," 2nd ed., Patty, F.A., ed., New York, John Wiley & Sons, Inc., 1958-63Vol. 2, Pg. 1897, 1963. | |
| guinea pig | LDLo | subcutaneous | 1500mg/kg (1500mg/kg) | FAO Nutrition Meetings Report Series. Vol. 44A, Pg. 63, 1967. | |
| human | LDLo | oral | 506mg/kg (506mg/kg) | "Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals", 11th ed., Rahway, NJ 07065, Merck & Co., Inc. 1989Vol. 11, Pg. 961, 1989. | |
| infant | LDLo | oral | 1480mg/kg (1480mg/kg) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION GASTROINTESTINAL: NAUSEA OR VOMITING | American Journal of the Medical Sciences. Vol. 193, Pg. 772, 1937. |
| man | LDLo | oral | 101mg/kg (101mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: NAUSEA OR VOMITING | American Journal of the Medical Sciences. Vol. 193, Pg. 772, 1937. |
| man | LDLo | oral | 1329mg/kg (1329mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: COMA BLOOD: HEMORRHAGE | Clinical Toxicology. Vol. 6, Pg. 189, 1973. |
| man | LDLo | unreported | 522mg/kg (522mg/kg) | "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970. | |
| mouse | LD50 | oral | 1110mg/kg (1110mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 132, Pg. 207, 1961. | |
| rabbit | LD50 | oral | 1300mg/kg (1300mg/kg) | Food and Cosmetics Toxicology. Vol. 16, Pg. 821, 1978. | |
| rabbit | LDLo | subcutaneous | 4250mg/kg (4250mg/kg) | Food and Cosmetics Toxicology. Vol. 16, Pg. 821, 1978. | |
| rat | LD50 | oral | 887mg/kg (887mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964. |
| women | LDLo | oral | 355mg/kg (355mg/kg) | BEHAVIORAL: COMA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION GASTROINTESTINAL: NAUSEA OR VOMITING | American Journal of the Medical Sciences. Vol. 193, Pg. 772, 1937. |
Hazard Codes: 
Xn
Risk Statements: 22-36/38-36/37/38
R22:Harmful if swallowed.
R36/38:Irritating to eyes and skin.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-24/25
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S24/25:Avoid contact with skin and eyes.
RIDADR: 3082
WGK Germany: 1
RTECS: VO4725000
F: 8
HazardClass: 6.1(b)
PackingGroup: III
Hazardous Substances Data: 119-36-8(Hazardous Substances Data)
6. Preparation of Methyl salicylate
Methyl salicylate can be produced by esterifying salicylic acid with methanol. Commercial methyl salicylate is now synthesized, but in the past, it was commonly distilled from the twigs of Betula lenta (sweet birch) and Gaultheria procumbens.
7. Use of Methyl salicylate
Methyl salicylate is commonly used as spices of food, toothpaste and cosmetics.It is also used to produce antalgesic drugs, pesticides, rubbing agent, ink, etc. Methyl Salicylate is used in flavoring for foods, candies, beverages and pharmaceuticals. It is used as a perfumery like magnolia, meadowsweet, root beer. It is also an odorant, perfume and ultraviolet absorber in cosmetics. This compound is used in medicine mainly for dephlogistication, analgesia. It is used in liniments and ointments for the relief of pain of lumbago, sciatica and rheumatics.
