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C80857

Sigma-Aldrich

trans-Cinnamic acid

≥99%

Synonym(s):

trans-3-Phenylacrylic acid, Cinnamic acid

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About This Item

Linear Formula:
C6H5CH=CHCOOH
CAS Number:
140-10-3
Molecular Weight:
148.16
Beilstein:
1905952
EC Number:
205-398-1
MDL number:
MFCD00004369
UNSPSC Code:
12352100
PubChem Substance ID:
24893022
NACRES:
NA.22

Quality Level

100

Assay

≥99%

form

crystals

bp

300 °C (lit.)

mp

132-135 °C (lit.)

SMILES string

OC(=O)\C=C\c1ccccc1

InChI

1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+

InChI key

WBYWAXJHAXSJNI-VOTSOKGWSA-N

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Application

trans-Cinnamic acid can be used in the synthesis of:
  • A trans-cinnamic acid hydrazide derivative with potent anti-mycobacterial activity.
  • Cinnamate glycerides via homogeneous esterification reaction.
  • Styrene via biocatalytic decarboxylation by plant cell cultures.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 1

Flash Point(F)

320.0 °F - closed cup

Flash Point(C)

160 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR9228
0000331389
SHBQ0672
SHBR1011
SHBR1681

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Homogeneous catalytic esterification of glycerol with cinnamic and methoxycinnamic acids to cinnamate glycerides in solventless medium: Kinetic modeling.
Molinero L, et al.
Chemical Engineering Journal, 247(2), 174-182 (2014)
Synthesis and antimycobacterial evaluation of new trans-cinnamic acid hydrazide derivatives.
Carvalho SA, et al.
Bioorganic & Medicinal Chemistry, 18(2), 538-541 (2008)
M Takemoto et al.
Chemical & pharmaceutical bulletin, 49(5), 639-641 (2001-06-01)
A novel method for producing styrenes from trans-cinnamic acids was developed. When trans-cinnamic acid was incubated with plant cell cultures at room temperature, styrene was obtained. 4-Hydroxy-3-methoxystyrene (2a), 3-nitrostyrene (2f) and furan (2g) were synthesized quantitatively.
Bianca C Pérez et al.
Journal of medicinal chemistry, 56(2), 556-567 (2013-01-01)
The control of malaria is challenged by drug resistance, and new antimalarial drugs are needed. New drug discovery efforts include consideration of hybrid compounds as potential multitarget antimalarials. Previous work from our group has demonstrated that hybrid structures resulting from
Stanislava Gorjanović et al.
Journal of agricultural and food chemistry, 60(38), 9573-9580 (2012-09-07)
Hydrogen peroxide scavenging (HPS) activity of unfermented (green, yellow, and white), partially fermented (oolong), and completely fermented (black) tea ( Camellia sinensis ), maté ( Ilex paraguariensis ), and various herbal infusions, as well as individual compounds (flavan-3-ols, flavonols, cinnamic
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