Sinapaldehyde information

Sinapaldehyde
Names
	Systematic IUPAC name (E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enal
	Other names (trans)-3,5-Dimethoxy-4-hydroxycinnamaldehyde; Sinapic aldehyde; Sinapinaldehyde; Sinapoyl aldehyde; Sinapyl aldehyde; ;
Identifiers
CAS Number	4206-58-0;
3D model (JSmol)	Interactive image;
3DMet	B00807;
Beilstein Reference	2215799
ChEBI	CHEBI:27949;
ChEMBL	ChEMBL225067 ;
ChemSpider	4444359 ;
ECHA InfoCard	100.156.065
EC Number	627-731-3;
KEGG	C05610;
MeSH	Sinapaldehyde
PubChem CID	5280802;
CompTox Dashboard (EPA)	DTXSID201016569 ;
	InChI 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+ Key: CDICDSOGTRCHMG-ONEGZZNKSA-N;
	SMILES COC1=CC(=CC(=C1O)OC)/C=C/C=O;
Properties
Chemical formula	C11H12O4
Molar mass	208.213 g·mol−1
Melting point	104 to 106 °C (219 to 223 °F; 377 to 379 K)
log P	1.686
Acidity (pKa)	9.667
Basicity (pKb)	4.330
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Related compounds
Related alkenals	Cinnamaldehyde; Coniferyl aldehyde; DMACA reagent; 2-Nitrocinnamaldehyde
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Sinapaldehyde is an organic compound with the formula HO(CH₃O)₂C₆H₂CH=CHCHO. It is a derivative of cinnamaldehyde, featuring one hydroxy group and two methoxy groups as substituents. It is an intermediate in the formation of sinapyl alcohol, a lignol that is a major precursor to lignin.^[3]^[4]

^ "AC1L3OEQ - Compound Summary". The PubChem Project. USA: National Center for Biotechnology Information.
^ "C&L Inventory". www.echa.europa.eu.
^ Wout Boerjan, John Ralph, Marie Baucher "Lignin Biosynthesis" Annu. Rev. Plant Biol. 2003, vol. 54, pp. 519–46. doi:10.1146/annurev.arplant.54.031902.134938
^ Li, Laigeng; Cheng, Xiao Fei; Leshkevich, Jacqueline; Umezawa, Toshiaki; Harding, Scott A.; Chiang, Vincent L. (2001). "The Last Step of Syringyl Monolignol Biosynthesis in Angiosperms is Regulated by a Novel Gene Encoding Sinapyl Alcohol Dehydrogenase". The Plant Cell. 13 (7): 1567–1586. doi:10.1105/tpc.010111. PMC 139549. PMID 11449052.

[1] "AC1L3OEQ - Compound Summary". The PubChem Project. USA: National Center for Biotechnology Information.

[2] "C&L Inventory". www.echa.europa.eu.

[3] Wout Boerjan, John Ralph, Marie Baucher "Lignin Biosynthesis" Annu. Rev. Plant Biol. 2003, vol. 54, pp. 519–46. doi:10.1146/annurev.arplant.54.031902.134938

[TPC-4] Li, Laigeng; Cheng, Xiao Fei; Leshkevich, Jacqueline; Umezawa, Toshiaki; Harding, Scott A.; Chiang, Vincent L. (2001). "The Last Step of Syringyl Monolignol Biosynthesis in Angiosperms is Regulated by a Novel Gene Encoding Sinapyl Alcohol Dehydrogenase". The Plant Cell. 13 (7): 1567–1586. doi:10.1105/tpc.010111. PMC 139549. PMID 11449052.

Sinapaldehyde information

and 13 Related for: Sinapaldehyde information

Sinapaldehyde

Sinapyl alcohol

Syringaldehyde

Sinapinic acid

Senra incana

Syringol

Coniferyl aldehyde

Syringic acid

Sinapine

Acetosyringone

C11H12O4

Canolol

Dictionary of natural phenols and polyphenols molecular formulas

Names

Systematic IUPAC name (E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enal^[1]
Other names (trans)-3,5-Dimethoxy-4-hydroxycinnamaldehyde Sinapic aldehyde Sinapinaldehyde Sinapoyl aldehyde Sinapyl aldehyde
Identifiers
CAS Number	4206-58-0
3D model (JSmol)	Interactive image
3DMet	B00807
Beilstein Reference	2215799
ChEBI	CHEBI:27949
ChEMBL	ChEMBL225067^Y
ChemSpider	4444359^Y
ECHA InfoCard	100.156.065
EC Number	627-731-3
KEGG	C05610
MeSH	Sinapaldehyde
PubChem CID	5280802
CompTox Dashboard (EPA)	DTXSID201016569
InChI 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+ Key: CDICDSOGTRCHMG-ONEGZZNKSA-N
SMILES COC1=CC(=CC(=C1O)OC)/C=C/C=O
Properties
Chemical formula	C₁₁H₁₂O₄
Molar mass	208.213 g·mol⁻¹
Melting point	104 to 106 °C (219 to 223 °F; 377 to 379 K)
log P	1.686
Acidity (pK_a)	9.667
Basicity (pK_b)	4.330
Hazards
GHS labelling:^[2]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Related compounds
Related alkenals	Cinnamaldehyde Coniferyl aldehyde DMACA reagent 2-Nitrocinnamaldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references