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404586

Sinapyl alcohol

Name: Sinapyl alcohol
Brand: ALDRICH

technical grade, 80%

Synonym(s):

4-Hydroxy-3,5-dimethoxycinnamyl alcohol

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About This Item

Linear Formula:

HOC₆H₂(OCH₃)₂CH=CHCH₂OH

CAS Number:

537-33-7

Molecular Weight:

210.23

NACRES:

NA.22

PubChem Substance ID:

24865257

UNSPSC Code:

12352100

MDL number:

MFCD00192441

Assay:

80%

Form:

solid

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Properties

grade

technical grade

Quality Level

100

assay

80%

form

solid

mp

61-65 °C (lit.)

functional group

hydroxyl

storage temp.

2-8°C

SMILES string

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

InChI

1S/C11H14O4/c1-14-9-6-8(4-3-5-12)7-10(15-2)11(9)13/h3-4,6-7,12-13H,5H2,1-2H3/b4-3+

InChI key

LZFOPEXOUVTGJS-ONEGZZNKSA-N

Description

General description

Sinapyl alcohol, a monolignol, is a primary lignin monomer. It has been evaluated for anti-inflammatory and antinociceptive activities. It participates in the initial stages in the biosynthesis of lignin. Coupling reactions of sinapyl alcohol and sinapyl p-hydroxybenzoate has been reported. Preparation of sinapyl alcohol by selective 1,2-reduction of corresponding cinnamate esters using diisobutylaluminium hydride as reducing agent has been studied.

Application

Sinapyl alcohol may be employed in the preparation of lignin, a highly stable biopolymer.

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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A possible mechanism for the oxidation of sinapyl alcohol by peroxidase-dependent reactions in the apoplast: enhancement of the oxidation by hydroxycinnamic acids and components of the apoplast.

Takahama U, et al.

Plant Physiology, 37(4), 499-504 (1996)

Enzymatic activities for lignin monomer intermediates highlight the biosynthetic pathway of syringyl monomers in Robinia pseudoacacia.

Jun Shigeto et al.

Journal of plant research, 130(1), 203-210 (2016-11-27)

Most of the known 4-coumarate:coenzyme A ligase (4CL) isoforms lack CoA-ligation activity for sinapic acid. Therefore, there is some doubt as to whether sinapic acid contributes to sinapyl alcohol biosynthesis. In this study, we characterized the enzyme activity of a

Identification and characterisation of Arabidopsis glycosyltransferases capable of glucosylating coniferyl aldehyde and sinapyl aldehyde.

Eng-Kiat Lim et al.

FEBS letters, 579(13), 2802-2806 (2005-05-24)

This study describes the substrate recognition profile of UGT72E1, an UDP-glucose:glycosyltransferase of Arabidopsis thaliana that is the third member of a branch of glycosyltransferases, capable of conjugating lignin monomers and related metabolites. The data show that UGT72E1, in contrast to

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Global Trade Item Number

SKU	GTIN
404586-100MG	04061831986938