404586
Sinapyl alcohol
technical grade, 80%
Sinónimos:
4-Hydroxy-3,5-dimethoxycinnamyl alcohol
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Fórmula lineal:
HOC6H2(OCH3)2CH=CHCH2OH
Número CAS:
Peso molecular:
210.23
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
80%
Form:
solid
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Permítanos ayudarleInChI
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+
SMILES string
COc1cc(\C=C\CO)cc(OC)c1O
InChI key
LZFOPEXOUVTGJS-ONEGZZNKSA-N
grade
technical grade
assay
80%
form
solid
mp
61-65 °C (lit.)
functional group
hydroxyl
storage temp.
2-8°C
Quality Level
Categorías relacionadas
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Clase de almacenamiento
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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
Toshiyuki Tanaka et al.
Plant physiology, 178(2), 552-564 (2018-08-22)
Green leaf volatiles (GLVs), including six-carbon (C6) aldehydes, alcohols, and esters, are formed when plant tissues are damaged. GLVs play roles in direct plant defense at wound sites, indirect plant defense via the attraction of herbivore predators, and plant-plant communication.
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
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)
Guilhem Reyt et al.
Nature communications, 12(1), 2320-2320 (2021-04-21)
Lignin is a complex polymer deposited in the cell wall of specialised plant cells, where it provides essential cellular functions. Plants coordinate timing, location, abundance and composition of lignin deposition in response to endogenous and exogenous cues. In roots, a
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