A phenylpropanoid with diverse biological activities
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Sinapaldehyde

Item No. 40267

Technical Information
Formal Name
3-(4-hydroxy-3,5-dimethoxyphenyl)-2E-propenal
CAS Number
4206-58-0
Synonyms
  • Sinapylaldehyde
  • trans-Sinapaldehyde
Molecular Formula
C11H12O4
Formula Weight
Purity
≥98%
A solid
DMSO: SolubleMethanol: Soluble
SMILES
O=C/C=C/C1=CC(OC)=C(C(OC)=C1)O
InChi Code
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
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Sinapaldehyde is a phenylpropanoid that has been found in A. altissima and has diverse biological activities.1,2,3,4,5,6 It is an intermediate in the biosynthesis of the monolignol sinapyl alcohol (Item No. 33916) in angiosperms.2 Sinapaldehyde is an inhibitor of farnesyltransferase (FTase; IC50 = 23.99 µM for the rat enzyme).3 It inhibits TNF-α-induced NF-κB transcriptional activity in a reporter assay using HepG2 cells (IC50 = 13.25 µM) and reduces LPS-induced nitric oxide (NO) production in RAW 264.7 cells (IC50 = 5.92 µM).1,4 Sinapaldehyde scavenges DPPH (Item No. 14805) and ABTS (Item No. 27317) radicals in cell-free assays (IC50s = 83.02 and 43.15 µM, respectively).5 It is active against the Gram-positive bacteria P. pseudomonas, E. coli, and S. enterica (MICs = 64, 128, and 128 µg/ml, respectively) and the Gram-negative bacteria B. cereus, methicillin-sensitive S. aureus (MSSA), and methicillin-resistant S. aureus (MRSA; MICs = 128, 64, and 128 µg/ml, respectively).6 It also inhibits α-glucosidase with an IC50 value of 98.81 µM.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kim, H.M., Lee, J.S., Sezirahiga, J., et alA new canthinone-type alkaloid isolated from Ailanthus altissima swingle. Molecules 21(5), 642 (2016).

    2. Li, L., Cheng, X.F., Leshkevich, J., et alThe last step of syringyl monolignol biosynthesis in angiosperms is regulated by a novel gene encoding sinapyl alcohol dehydrogenase. Plant Cell 13(7), 1567-1586 (2001).

    3. Sung, N.-D., Cho, Y.K., Kwon, B.M., et al3D QSAR studies on cinnamaldehyde analogues as farnesyl protein transferase inhibitors. Arch. Pharm. Res. 27(10), 1001-1008 (2004).

    4. Sun, Y.N., Li, W., Song, S.B., et alNF-κB inhibitory activities of phenolic and lignan components from the stems of Acanthopanax divaricatus var. albeofructus. Nat. Prod. Sci. 20(4), 232-236 (2014).

    5. Liu, L., Zou, M., Yin, Q., et alPhenylpropanoids from Liparis nervosa and their in vitro antioxidant and α-glucosidase inhibitory activities. Med. Chem. Res. 30, 1005-1010 (2021).

    6. Lakornwong, W., Kanokmedhakul, K., and Kanokmedhakul, S. A new coruleoellagic acid derivative from stems of Rhodamnia dumetorum. Nat. Prod. Res. 32(14), 1653-1659 (2018).