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Merck

67563

Sigma-Aldrich

3,4-Dihydroxy-5-methoxy-zimtsäure

≥95.0% (HPLC)

Synonym(e):

3-(3,4-Dihydroxy-5-methoxy-phenyl)-2-propensäure, 3-Methoxy-kaffeesäure, 5-Hydroxy-ferulasäure

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About This Item

Empirische Formel (Hill-System):
C10H10O5
CAS-Nummer:
Molekulargewicht:
210.18
Beilstein:
2697317
MDL-Nummer:
UNSPSC-Code:
12352106
PubChem Substanz-ID:
NACRES:
NA.25

Assay

≥95.0% (HPLC)

Form

solid

Anwendung(en)

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+

InChIKey

YFXWTVLDSKSYLW-NSCUHMNNSA-N

Biochem./physiol. Wirkung

Secondary plant metabolite of the phenylpropanoid pathway.

Verpackung

Bottomless glass bottle. Contents are inside inserted fused cone.

Piktogramme

Exclamation mark

Signalwort

Warning

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

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
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
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
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)
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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