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| | Methyl phenylacetate Basic information |
| | Methyl phenylacetate Chemical Properties |
| Melting point | 107-115 °C | | Boiling point | 218 °C (lit.) | | density | 1.066 g/mL at 20 °C (lit.) | | vapor pressure | 16.9-75Pa at 20℃ | | FEMA | 2733 | METHYL PHENYLACETATE | | refractive index | n20/D 1.503(lit.) | | Fp | 195 °F | | storage temp. | Store below +30°C. | | solubility | Chloroform (Slightly), Methanol (Slightly) | | form | neat | | color | Colourless | | Odor | at 10.00 % in dipropylene glycol. sweet floral honey spice waxy almond | | Odor Type | honey | | Water Solubility | Miscible with water. | | Merck | 14,7268 | | JECFA Number | 1008 | | BRN | 878795 | | Stability: | Stable. Combustible. Incompatible with strong oxidizing agents, strong bases. | | InChIKey | CRZQGDNQQAALAY-UHFFFAOYSA-N | | LogP | 1.91-2.09 at 21.9-25℃ | | CAS DataBase Reference | 101-41-7(CAS DataBase Reference) | | NIST Chemistry Reference | Benzeneacetic acid, methyl ester(101-41-7) | | EPA Substance Registry System | Methyl phenylacetate (101-41-7) |
| Hazard Codes | Xn | | Risk Statements | 21-R21 | | Safety Statements | 23-24/25 | | WGK Germany | 2 | | RTECS | AJ3175000 | | TSCA | Yes | | HS Code | 29163500 | | Hazardous Substances Data | 101-41-7(Hazardous Substances Data) | | toxicity | The acute oral LD50 in rats was reported as 2.55 g/kg (1.67-3.43 g/kg) and the acute dermal LD50 in rabbits as 2.4 g/kg (0.15-4.7 g/kg) (Moreno, 1974). |
| | Methyl phenylacetate Usage And Synthesis |
| Description | Methyl phenylacetate belongs to an ester compound form between the methanol and phenylacetate. It chemical formula is C6H5CH2COOCH3. It is generally found in brandy, capsicum, honey, pepper, some wine, coca and coca products. It is mainly used as a flavouring agent, and is also supplemented into perfumes to enhance honey scents. It can also be used as the precursor for the manufacture of synthetic perfumes. In addition, as an acylating agent, it can participate in the enantioselective acylation reaction of beta-lactam intermediate catalyzed by the penicillin G amidase. | | Chemical Properties | Methyl phenylacetate is a clear colorless liquid that is only slightly soluble in water, but very soluble in most organic solvents. It has a strong odor similar to honey. The odor is so strong that recommended smelling is of a solution with 10% or less methyl phenyl acetate. This compound also naturally occurs in brandy, capsicum, coffee, honey, pepper and some wine. | | Occurrence | Reported found in cocoa, coffee, strawberry, pineapple, pepper, hop oil, cognac, peanut, honey, starfruit,
Bourbon vanilla, mountain papaya, roasted chicory root and rooibus tea (Aspalathus linearis).
| | Uses | Methyl phenylacetate is utilized for partition coefficient measurement experiments. It is mainly used in the flavor industry and in perfumes to impart honey scents. Further, it acts as a precursor to prepare synthetic perfumes. It acts as an acylating agent and involved in the enantioselective acylation of beta-lactam intermediate using penicillin G amidase. | | Application | Methyl Phenylacetate is used as a reagent in the synthesis of various organic reactions, one of which is the synthesis of Vulpinic Acid; a lichen metabolite with anti-inflammatory properties. It is also used in the formulation of edible flavors, for the preparation of honey, chocolate, tobacco and other flavors; it can also be used in daily chemical flavors for the preparation of rose, oriental flavors and other flavors. IFRA has no restrictions. | | Definition | ChEBI: Methyl benzeneacetate is a member of benzenes. It is a flavoring ingredient. Odoriferous constituent of many plants. | | Preparation | Methyl phenylacetate is synthesized from phenylacetonitrile by hydrolysis and esterification. Put methanol into a dry glass-lined reaction pot, stir and cool to below 30°C, add sulfuric acid dropwise, heat up to 90°C after adding, and start adding phenylacetonitrile dropwise, control the temperature at about 95°C, and finish adding in 1.5h. After reacting at 95-100 °C for 6 h, it was cooled to below 40 °C and diluted with water equivalent to about 0.6 times the reaction solution. The acid water was separated by standing, and a saturated sodium carbonate solution was added for neutralization and washing, and the aqueous layer was discarded. It is dehydrated with anhydrous calcium chloride and fractionated under reduced pressure to obtain methyl phenylacetate with a yield of 80%. | | Aroma threshold values | Detection: 25 ppb | | Taste threshold values | Taste characteristics at 30 ppm: floral, fruity, honey, spice, waxy and sweet | | Synthesis Reference(s) | Journal of the American Chemical Society, 93, p. 4919, 1971 DOI: 10.1021/ja00748a051
Tetrahedron Letters, 30, p. 2945, 1989 DOI: 10.1016/S0040-4039(00)99165-2 | | General Description | Methyl phenylacetate has been identified in the volatile fraction of beewax absolute oil, dried fruiting bodies of Boletus auripes, Chinese fermented black soybeans and peated malt. | | Biochem/physiol Actions | Methyl phenylacetate undergoes decomposition on photolysis in methanol. Methyl phenylacetate acts as acylating agent and causes the enantioselective acylation of beta-lactam intermediate using penicillin G amidase. Methyl phenylacetate is the starting material in manufacture of synthetic perfumes. | | Safety Profile | Moderately toxic by
ingestion and skin contact. A skin irritant.
Combustible liquid. When heated to
decomposition it emits acrid smoke and
irritating fumes. See also ESTERS. |
| | Methyl phenylacetate Preparation Products And Raw materials |
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