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Key Documents

67563

Sigma-Aldrich

3,4-Dihydroxy-5-methoxycinnamic acid

≥95.0% (HPLC)

Synonym(s):

3-(3,4-Dihydroxy-5-methoxyphenyl)-2-propenoic acid, 3-Methoxycaffeic acid, 5-Hydroxyferulic acid

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About This Item

Empirical Formula (Hill Notation):
C10H10O5
CAS Number:
Molecular Weight:
210.18
Beilstein:
2697317
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.25

Quality Level

Assay

≥95.0% (HPLC)

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

SMILES string

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

InChI

1S/C10H10O5/c1-15-8-5-6(2-3-9(12)13)4-7(11)10(8)14/h2-5,11,14H,1H3,(H,12,13)/b3-2+

InChI key

YFXWTVLDSKSYLW-NSCUHMNNSA-N

Biochem/physiol Actions

Secondary plant metabolite of the phenylpropanoid pathway.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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C C Chapple et al.
The Plant cell, 4(11), 1413-1424 (1992-11-01)
Mutants of Arabidopsis deficient in a major leaf phenylpropanoid ester, 2-O-sinapoyl-L-malate, were identified by thin-layer chromatographic screening of methanolic leaf extracts from several thousand mutagenized plants. Mutations at a locus designated SIN1 also eliminate accumulation of the sinapic acid esters
S Maury et al.
Plant physiology, 121(1), 215-224 (1999-09-11)
The biosynthesis of lignin monomers involves two methylation steps catalyzed by orthodiphenol-O-methyltransferases: caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferases (COMTs) and caffeoyl-coenzyme A (CoA)/5-hydroxyferuloyl-CoA 3/5-O-methyltransferases (CCoAOMTs). Two COMT classes (I and II) were already known to occur in tobacco (Nicotiana tabacum) and three
K Inoue et al.
Archives of biochemistry and biophysics, 375(1), 175-182 (2000-02-23)
Caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase (COMT, EC 1.2.1.68) catalyzes at least two reactions in lignin biosynthesis. Of its two supposed substrates in the lignin pathway, COMT from most sources methylates 5-hydroxyferulic acid (5HFA) with two to three times higher activity than
I Muzac et al.
Archives of biochemistry and biophysics, 375(2), 385-388 (2000-03-04)
We report that the cDNA clone (Accession No. U70424), previously isolated from Arabidopsis thaliana as encoding a caffeic acid/5-hydroxyferulic acid O-methyltransferase (OMT) (1), has now been overexpressed in Escherichia coli BL21 and its recombinant protein identified as a novel flavonol
R C Bugos et al.
Phytochemistry, 31(5), 1495-1498 (1992-05-01)
Bispecific O-methyltransferase (OMT, EC 2.1.1.68) which catalyses the meta-specific methylation of caffeic acid and 5-hydroxyferulic acid was purified to homogeneity from the developing secondary xylem of aspen (Populus tremuloides). The enzyme was purified by conventional techniques and affinity chromatography on

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