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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:
1782-55-4
Molecular Weight:
210.18
Beilstein:
2697317
MDL number:
MFCD03002791
UNSPSC Code:
12352106
PubChem Substance ID:
329760617
NACRES:
NA.25
Pricing and availability is not currently available.

Quality Level

100

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

Related Categories

Biochem/physiol Actions

Secondary plant metabolite of the phenylpropanoid pathway.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCBJ6821V
BCBJ6821

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John M Humphreys et al.
Current opinion in plant biology, 5(3), 224-229 (2002-04-19)
Considerable interest in lignin biosynthesis has been fueled by the many roles that lignin plays in development and in resistance to biotic and abiotic stress, as well as its importance to industry and agriculture. Although the pathway leading to the
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
Probing the mysteries of lignin biosynthesis: the crystal structure of caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase provides new insights.
Nancy A Eckardt
The Plant cell, 14(6), 1185-1189 (2002-06-27)
L Li et al.
The Journal of biological chemistry, 275(9), 6537-6545 (2000-02-29)
S-Adenosyl-L-methionine-dependent caffeate O-methyltransferase (COMT, EC 2.1.1.6) has traditionally been thought to catalyze the methylation of caffeate and 5- hydroxyferulate for the biosynthesis of syringyl monolignol, a lignin constituent of angiosperm wood that enables efficient lignin degradation for cellulose production. However
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