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Merck
CN

382159

Sigma-Aldrich

trans-3,5-Dimethoxy-4-hydroxycinnamaldehyde

98%

Synonym(s):

Sinapinaldehyde

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About This Item

Linear Formula:
HOC6H2(OCH3)2CH=CHCHO
CAS Number:
4206-58-0
Molecular Weight:
208.21
MDL number:
MFCD00075980
UNSPSC Code:
12352100
PubChem Substance ID:
24863871

Key Documents

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Assay

98%

form

solid

mp

104-106 °C (lit.)

storage temp.

2-8°C

SMILES string

[H]C(=O)\C([H])=C(/[H])c1cc(OC)c(O)c(OC)c1

InChI

1S/C11H12O4/c1-14-9-6-8(4-3-5-12)7-10(15-2)11(9)13/h3-7,13H,1-2H3/b4-3+

InChI key

CDICDSOGTRCHMG-ONEGZZNKSA-N

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Application

trans-3,5-Dimethoxy-4-hydroxycinnamaldehyde (Sinapinaldehyde) is suitable for use in the determination of phenolic compounds by HPLC with multiple wavelength detector in grape marc distillates aged in Quercus petraea, Quercus robur and Quercus alba wooden barrels. It is suitable for use in the GC/MS positive ion chemical ionization (PICI) characterization of volatile phenols and benzene aldehydes in various woods.

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000071979
0000071980
0000057913
0000070684
0000070683

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Catherine Lapierre et al.
Phytochemistry, 65(3), 313-321 (2004-01-31)
A series of transgenic poplars down-regulated for cinnamyl alcohol dehydrogenase (CAD) was analyzed by thioacidolysis. Among the lignin-derived monomers, the indene compounds that were recently shown to originate from sinapaldehyde incorporated into lignins through 8-O-4-cross-coupling, were found to increase as
Ramesh B Nair et al.
The Plant cell, 16(2), 544-554 (2004-01-20)
Recent research has significantly advanced our understanding of the phenylpropanoid pathway but has left in doubt the pathway by which sinapic acid is synthesized in plants. The reduced epidermal fluorescence1 (ref1) mutant of Arabidopsis thaliana accumulates only 10 to 30%
Mutsumi Sugiura et al.
FEMS microbiology letters, 224(2), 285-290 (2003-08-02)
We characterized kinetics and substrate oxidation of a novel lignin peroxidase (YK-LiP) isolated from white-rot fungus Phanerochaete sordida YK-624. YK-LiP enzyme was identified and purified to homogeneity by anion-exchange chromatography and gel permeation chromatography. The molecular mass of YK-LiP was
Abdellah Barakate et al.
The Plant cell, 23(12), 4492-4506 (2011-12-14)
The manipulation of lignin could, in principle, facilitate efficient biofuel production from plant biomass. Despite intensive study of the lignin pathway, uncertainty exists about the enzyme catalyzing the last step in syringyl (S) monolignol biosynthesis, the reduction of sinapaldehyde to
Riccardo Flamini et al.
Journal of mass spectrometry : JMS, 42(5), 641-646 (2007-03-21)
Extracts from acacia, chestnut, cherry, mulberry, and oak wood, used in making barrels for aging wine and spirits were studied by GC/MS positive ion chemical ionization (PICI). Wood chips were extracted by a 50% water/ethanol solution and a tartrate buffer
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