(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% ^*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:

methyl 2-phenylhexahydro-2H-isoxazolo<2,3-a>pyridine-3-carboxylate

(2S,3S,3aS)-3-Phenyl-hexahydro-isoxazolo[2,3-a]pyridine-2-carboxylic acid methyl ester

methyl 2-phenylhexahydro-2H-isoxazolo<2,3-a>pyridine-3-carboxylate

methyl 2-phenylhexahydro-2H-isoxazolo<2,3-a>pyridine-3-carboxylate

Refernces

• 1、 Shuttleworth, Timothy A.,Miles-Hobbs, Alexandra M.,Pringle, Paul G.,Sparkes, Hazel A.. "2-Pyridyl substituents enhance the activity of palladium-phospha-adamantane catalysts for the methoxycarbonylation of phenylacetylene". . p. 125 - 137. Retrieved 2017.
• 2、 Galow, Trent H.,Drechsler, Ulf,Hanson, Jarrod A.,Rotello, Vincent M.. "Highly reactive heterogeneous Heck and hydrogenation catalysts constructed through 'bottom-up' nanoparticle self-assembly". . p. 1076 - 1077. Retrieved 2002.
• 3、 Matoba, Kazutaka,Motofusa, Shin-Ichi,Sik Cho, Chan,Ohe, Kouichi,Uemura, Sakae. "Palladium(II)-catalyzed phenylation of unsaturated compounds using phenylantimony chlorides under air". . p. 3 - 10. Retrieved 1999.
• 4、 Polshettiwar, Vivek,Hesemann, Peter,Moreau, Jo?l J.E.. "Silica hybrid material containing Pd-NHC complex as heterogeneous catalyst for Mizoroki-Heck reactions". . p. 5363 - 5366. Retrieved 2007.
• 5、 Xiong, Zhengchang,Wang, Nengdong,Dai, Mingji,Li, Ang,Chen, Jiahua,Yang, Zhen. "Synthesis of novel palladacycles and their application in heck and Suzuki reactions under aerobic conditions". . p. 3337 - 3340. Retrieved 2004.
• 6、 Makhubela, Banothile C.E.,Jardine, Anwar,Smith, Gregory S.. "Pd nanosized particles supported on chitosan and 6-deoxy-6-amino chitosan as recyclable catalysts for Suzuki-Miyaura and Heck cross-coupling reactions". . p. 231 - 241. Retrieved 2011.
• 7、 Liu, Ying,Feng, Xiu Juan,Bao, De Cai,Li, Kai Xiao,Bao, Ming. "Preparation of microcapsule-supported palladium catalyst using SPG (Shirasu Porous Glass) emulsification technique". . p. 979 - 982. Retrieved 2010.
• 8、 Takeda, Takanobu,Watanabe, Hidenori,Kitahara, Takeshi. "Direct Oxidation of Acetals and Aldehydes to Esters". . p. 1149 - 1150. Retrieved 1997.
• 9、 Lei, Lei. "Pd–Schiff base complex supported on Fe3O4 magnetic nanoparticles: A new and highly efficient reusable catalyst for C–C bond formation in water". . . Retrieved 2019.
• 10、 Mino, Takashi,Watanabe, Kohei,Abe, Taichi,Kogure, Taketo,Sakamoto, Masami. "Palladium-catalyzed Mizoroki-Heck type reaction with aryliodine diacetates using hydrazone ligand". . p. 2015 - 2021. Retrieved 2013.