| Identification | More | [Name]
2-Methoxycinnamic acid | [CAS]
6099-03-2 | [Synonyms]
2-METHOXYCINNAMIC ACID
3-(2-METHOXYPHENYL)ACRYLIC ACID
AKOS BBB/196
AKOS BBS-00007900
AURORA 11318
METHOXYCINNAMIC ACID,2-
O-METHOXYCINNAMIC ACID
RARECHEM BK HC T255
TRANS-2-METHOXYCINNAMIC ACID
TRANS-3-(2-METHOXYPHENYL)ACRYLIC ACID
TRANS-O-METHYL-O-COUMARIC ACID
TRANS-O-METHYL-O-CUMARIC ACID
Cinnamic acid, o-methoxy-
(2E)-3-(2-methoxyphenyl)prop-2-enoic acid
2-Methoxycinnamic acid,predominantly trans
2-METHOXYCINNAMIC ACID, 98%, PREDOMINANTLY TRANS
2-Methoxycinnamic acid, 98+%
2-Propenoic acid, 3-(2-methoxyphenyl)-
3-(2-Methoxyphenyl)prop-2-enoic acid, 3-(2-Hydroxyphenyl)acrylic acid
(2E)-3-(2-methoxyphenyl)acrylic acid | [EINECS(EC#)]
228-047-4 | [Molecular Formula]
C10H10O3 | [MDL Number]
MFCD00064238 | [Molecular Weight]
178.18 | [MOL File]
6099-03-2.mol |
| Chemical Properties | Back Directory | [Appearance]
light yellow crystalline powder | [Melting point ]
182-186 °C | [Boiling point ]
250.41°C (rough estimate) | [density ]
1.1479 (rough estimate) | [refractive index ]
1.5088 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
powder | [pka]
pK1:4.462 (25°C) | [color ]
White | [BRN ]
2209714 | [InChI]
InChI=1S/C10H10O3/c1-13-9-5-3-2-4-8(9)6-7-10(11)12/h2-7H,1H3,(H,11,12) | [InChIKey]
FEGVSPGUHMGGBO-UHFFFAOYSA-N | [SMILES]
C(O)(=O)C=CC1=CC=CC=C1OC | [LogP]
2.418 (est) | [CAS DataBase Reference]
6099-03-2(CAS DataBase Reference) | [NIST Chemistry Reference]
2-Propenoic acid, 3-(2-methoxyphenyl)-(6099-03-2) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29189900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
light yellow crystalline powder | [Uses]
(E)-3-(2-Methoxyphenyl)acrylic Acid is a noncompetitive inhibitor of tyrosinase. | [Definition]
ChEBI: (E)-2-methoxycinnamic acid is a member of the class of cinnamic acids that is trans-cinnamic acid carrying a methoxy substituent at position 2 on the benzene ring. It has a role as a Brassica napus metabolite and an EC 1.14.18.1 (tyrosinase) inhibitor. It is a member of cinnamic acids and a monomethoxybenzene. It is functionally related to a trans-cinnamic acid. | [Synthesis]
To a 500 mL three-necked round-bottomed flask was added o-methoxybenzaldehyde (20 g, 146.90 mmol, 1.00 eq.), pyridine (250 mL), malonic acid (18.3 g, 175.86 mmol, 1.20 eq.) and piperidine (2.5 g, 29.36 mmol, 0.20 eq.). The reaction mixture was stirred at 85°C overnight. Upon completion of the reaction, most of the solvent was removed by distillation under reduced pressure, followed by adjusting the pH of the remaining solution with aqueous hydrochloric acid to 3.0. The precipitated solid was collected by filtration to afford 25.6 g (98% yield) of 2-methoxycinnamic acid as a white solid. | [References]
[1] Patent: WO2014/182950, 2014, A1. Location in patent: Paragraph 00322; 00323
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 336 - 343
[3] Journal of the Indian Chemical Society, 1988, vol. 65, # 3, p. 187 - 191
[4] Molecules, 2009, vol. 14, # 10, p. 4166 - 4179
[5] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 15, p. 4513 - 4519 |
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