(Z)-Methyl cinnamate

Base Information

• Chemical Name: (Z)-Methyl cinnamate
• CAS No.: 103-26-4
• Molecular Formula: C10H10O2
• Molecular Weight: 162.188
• Hs Code.: 29163990
• UNII: C8O8SZU001
• DSSTox Substance ID: DTXSID401031262
• Nikkaji Number: J192.733G
• Wikidata: Q27275326
• Mol file: 103-26-4.mol

Synonyms:(Z)-Methyl cinnamate;Methyl cis-cinnamate;Methyl cis-3-phenylacrylate;cis-Methyl 3-phenyl-2-propenoate;Methyl (Z)-cinnamate;Methyl cinnamate, (Z)-;19713-73-6;UNII-C8O8SZU001;(Z)-Methyl 3-phenylacrylate;C8O8SZU001;2-Propenoic acid, 3-phenyl-, methyl ester, (2Z)-;(Z)-3-phenyl-2-propenoic acid methyl ester;cis-methyl cinnamate;Methyl cinnamate, (E);Methyl (2E)-3-phenyl-2-propenoate;Methyl cinnamate, (Z);methyl (Z)-3-phenylacrylate;cis-cinnamic acid methyl ester;Methyl ester(e)-Cinnamic acid;(z)-cinnamic acid methyl ester;SCHEMBL2425288;FEMA 2698;CHEBI:194139;DTXSID401031262;Cinnamic acid, methyl ester, (Z);Cinnamic acid, methyl ester, cis-;(Z)-3-phenyl-acrylic acid methyl ester;(z)-3-phenylpropenoic acid, methyl ester;CINNAMIC ACID,METHYL ESTER (TRANS);3-Phenyl-methyl ester(E)-2-Propenoic acid;METHYL (2Z)-3-PHENYLPROP-2-ENOATE;3-Phenyl-methyl ester(2E)-2-propenoic acid;cis-3-phenyl-prop-2-enoic acid methyl ester;A800700;methyl (Z)-3-phenylprop-2-enoate;Methyl cinnamate;Q27275326

Chemical Property of (Z)-Methyl cinnamate

Chemical Property:

• Appearance/Colour: White to light yellow crystal or liquid
• Vapor Pressure: 0.0112mmHg at 25°C
• Melting Point: 33.5-36 °C
• Refractive Index: 1.5771
• Boiling Point: 261.9 °C at 760 mmHg
• Flash Point: 141.3 °C
• PSA: 26.30000
• Density: 1.078 g/cm³
• LogP: 1.87280
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: insoluble
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 162.068079557
• Heavy Atom Count: 12
• Complexity: 167

Purity/Quality:

99.0%Min ^*data from raw suppliers

Methyl cinnamate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C=CC1=CC=CC=C1
• Isomeric SMILES: COC(=O)/C=C\C1=CC=CC=C1
• Description: Methyl cinnamate is the methyl ester of cinnamic acid and is a white or transparent solid with a strong, aromatic odor. It is found naturally in a variety of plants, including in fruits, like strawberry, and some culinary spices, such as Sichuan pepper and some varieties of basil. Eucalyptus olida has the highest known concentrations of methyl cinnamate (98 %) with a 2 - 6 % fresh weight yield in the leaf and twigs. Methyl cinnamate is used in the flavor and perfume industries. The flavor is fruity and strawberry-like; and the odor is sweet, balsamic with fruity odor, reminiscent of cinnamon and strawberry. It is known to attract males of various orchid bees, such as Aglae caerulea. Methyl cinnamate crystals extracted using steam distillation from Eucalyptus olida.
• Uses: Methyl cinnamate is used as a fragrance ingredient in cosmetics and household products. Methyl cinnamate was used to inhibit monophenolase and diphenolase activity of mushroom tyrosinase and it also has antimicrobial ability. It is mainly is used in the flavor and perfume industries. It is known to attract males of various orchid bees, such as Aglae caerulea.

Technology Process of (Z)-Methyl cinnamate

There total 682 articles about (Z)-Methyl cinnamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

chloranil (118-75-2) + ((1R,2R)-1-Methoxy-2-phenyl-cyclopropoxy)-trimethyl-silane → 2,3,5,6-tetrachlorobenzene-1,4-diol (87-87-6) + Methyl cinnamate (103-26-4,1754-62-7) + 3-Phenyl-3-(2,3,5,6-tetrachloro-4-hydroxy-phenoxy)-propionic acid methyl ester

Guidance literature:

In tetrahydrofuran; for 1h; Heating;

DOI:10.1016/S0040-4039(00)73235-7

Reference yield: 81.0%

((1R,2R)-1-Methoxy-2-phenyl-cyclopropoxy)-trimethyl-silane → 2,3,5,6-tetrachlorobenzene-1,4-diol (87-87-6) + Methyl cinnamate (103-26-4,1754-62-7) + 3-Phenyl-3-(2,3,5,6-tetrachloro-4-hydroxy-phenoxy)-propionic acid methyl ester

Guidance literature:

With chloranil; In tetrahydrofuran; for 1h; Heating;

DOI:10.1016/S0040-4039(00)73235-7

Reference yield: 79.0%

(E)-3-phenylacrylic acid (140-10-3) + methyl salicylate (119-36-8,8024-54-2) → Methyl cinnamate (103-26-4,1754-62-7) + salicylic acid (69-72-7,25496-36-0,8052-31-1)

Guidance literature:

(E)-3-phenylacrylic acid; With potassium carbonate; In N,N-dimethyl acetamide; at 110 ℃; for 0.5h;

methyl salicylate; at 110 ℃; for 24h;

DOI:10.1055/s-0033-1340285

upstream raw materials:

methanol

cinnamonitrile

(E)-3-phenylacrylic acid

ethyl (E)-2-acetyl-3-oxo-5-phenylpent-4-enoate

Downstream raw materials:

3-phenyl-3-piperidinopropionic acid methyl ester

(+/-)-4t-phenyl-4,5-dihydro-1H-pyrazole-3,5r-dicarboxylic acid-3-ethyl ester-5-methyl ester

3,4-diphenyl-furazan 2-oxide

3,5t-diphenyl-4,5-dihydro-isoxazole-4r-carboxylic acid methyl ester

Refernces

ASYMMETRIC SYNTHESIS OF R-β-AMINO BUTANOIC ACID AND S-β-TYROSINE: HOMOCHIRAL LITHIUM AMIDE EQUIVALENTS FOR MICHAEL ADDITIONS TO α,β-UNSATURATED ESTERS.

10.1016/S0957-4166(00)82354-X

The research focuses on the asymmetric synthesis of homochiral β-amino acids, which are important components of various natural products and pharmaceutical compounds. The purpose is to develop a highly stereoselective method for synthesizing these compounds using homochiral lithium amide equivalents in Michael additions to α,β-unsaturated esters. Methyl E-cinnamate (11) is a key α,β-unsaturated ester used in this research. It serves as a Michael acceptor in the asymmetric synthesis of homochiral β-amino acids. Specifically, it reacts with the lithium amide derived from R-N-(α-methylbenzyl)amine (6) to form the Michael adduct 12 with high stereoselectivity (yielding a single diastereoisomer with >99% diastereomeric excess). This adduct 12 is then subjected to debenzylation to produce the homochiral methyl ester of S-β-tyrosine (13), which is further hydrolyzed to obtain S-β-tyrosine hydrochloride (14) with high enantiomeric purity. The use of methyl E-cinnamate is crucial for achieving the desired stereoselective addition and subsequent transformations, highlighting its importance in the synthesis of chiral β-amino acids.

N,N-dialkylated monophenolic trans-2-phenylcyclopropylamines: Novel central 5-hydroxytryptamine receptor agonists

10.1021/jm00396a014

This research aimed to synthesize and test N,N-dialkylated monophenolic derivatives of trans-2-phenylcyclopropylamine for their activity as central 5-hydroxytryptamine (5-HT) and dopamine (DA) receptor agonists. The study found that a hydroxy substituent in the 2- or 3-position of the phenyl ring was necessary for 5-HT-receptor stimulation, with N,N-diethyl or N,N-di-n-propyl substitution yielding the most potent 5-HT-receptor agonists. Notably, the 4-hydroxy and 3,4-dihydroxy derivatives were inactive at central DA and 5-HT receptors. The compounds were synthesized using various chemical reactions, including cyclopropanation, Curtius rearrangement, and reductive methylation, with starting materials such as methyl trans-cinnamates and ethyl diazoacetate.