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Key Documents

D7927

Sigma-Aldrich

Sinapic acid

≥98%, powder

Synonym(s):

3,5-Dimethoxy-4-hydroxycinnamic acid, 4-Hydroxy-3,5-dimethoxy-cinnamic acid, Sinapinic acid

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About This Item

Empirical Formula (Hill Notation):
C11H12O5
CAS Number:
Molecular Weight:
224.21
Beilstein/REAXYS Number:
2699118
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥98%

form

powder

mol wt

monoisotopic mol wt 224.06839 Da

mp

~202 °C

solubility

H2O: slightly soluble (lit.)(lit.)
methanol: water: soluble (lit.)(lit.)
polar organic solvents: soluble (lit.)(lit.)

SMILES string

COc1cc(\C=C\C(O)=O)cc(OC)c1O

InChI

1S/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)/b4-3+

InChI key

PCMORTLOPMLEFB-ONEGZZNKSA-N

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General description

Sinapic acid is an hydroxycinnamic acid derivative that occurs naturally in Brassicaceae species .

Sinapic acid is a phenylpropanoid derivative that acts as a radical scavenger with antioxidant, antimicrobial, anti-inflammatory, and anticancer properties.

Application

Sinapic acid can be used:
  • As a potent peroxynitrite (ONOO−) oxidant scavenger for the protection of the cellular constituents against peroxynitrite cytotoxic species.
  • In the synthesis of antioxidant hydroxycinnamic acid xylan esters via esterification reaction.
  • In the synthesis of pseudo-cinnamic derivatives effective against mycobacterium tuberculosis.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sinapic acid: is it safe for humans?
Hasan H et al.
FABAD Journal of Pharmaceutical Sciences, 41, 39-39 (2016)
Urska Repnik et al.
The Journal of biological chemistry, 290(22), 13800-13811 (2015-04-03)
Cysteine cathepsins are primarily lysosomal proteases involved in general protein turnover, but they also have specific proteolytic functions in antigen presentation and bone remodeling. Cathepsins are most stable at acidic pH, although growing evidence indicates that they have physiologically relevant
Jin-Feng Huang et al.
Journal of inflammation research, 13, 883-895 (2020-11-20)
Low back pain (LBP) is a very common condition and leads to serious pain, disability, and price tag all over the world. Intervertebral disk degeneration (IDD) is one of the major reasons that contributed to LBP. The levels of interleukin
Synthesis and antioxidant activity of hydroxycinnamic acid xylan esters.
Wrigstedt P, et al.
Journal of Agricultural and Food Chemistry, 58(11), 6937-6943 (2010)
Synthesis and evaluation of a novel series of pseudo-cinnamic derivatives as antituberculosis agents.
Yoya GK, et al.
Bioorganic & Medicinal Chemistry, 19(2), 341-343 (2009)

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