Sinapyl Alcohol

• CAT Number: I036301
• CAS Number: 537-33-7
• Molecular Formula: C11H14O4
• Molecular Weight: 210.23
• Purity: 98%
• Synonyms: Sinapyl Alcohol
• Target: COX
• Solubility: To be determined
• Appearance: Solid powder
• Storage: 2-8°C
• IUPAC Name: (E)-4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenol
• InChI: 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+
• InChIKey: LZFOPEXOUVTGJS-ONEGZZNKSA-N
• SMILES: OC1=C(C=C(C=C1OC)/C=C/CO)OC

Sinapyl alcohol（Cat No.:I036301）, a monolignol found in Populus alba, serves as an aglycone form of syringin with anti-inflammatory and antinociceptive properties. As a precursor in lignin biosynthesis, it has been studied for its pharmacological effects. Sinapyl alcohol demonstrates the ability to reduce nitrite, prostaglandin E2 (PGE2), and TNF-α production induced by lipopolysaccharide (LPS) in RAW 264.7 cells at concentrations of 50, 100, and 200 µM.

Reference

1: Zhu X, Jiang L, Cai Y, Cao Y. Functional analysis of four Class III peroxidases from Chinese pear fruit: a critical role in lignin polymerization. Physiol Mol Biol Plants. 2021 Mar;27(3):515-522. doi: 10.1007/s12298-021-00949-9. Epub 2021 Feb 20. PMID: 33854280; PMCID: PMC7981345.
2: Elder T, Rencoret J, Del Río JC, Kim H, Ralph J. Radical Coupling Reactions of Hydroxystilbene Glucosides and Coniferyl Alcohol: A Density Functional Theory Study. Front Plant Sci. 2021 Mar 2;12:642848. doi: 10.3389/fpls.2021.642848. PMID: 33737945; PMCID: PMC7960926.
3: Simon C , Lion C , Ahouari H , Vezin H , Hawkins S , Biot C . Correction: EPR imaging of sinapyl alcohol and its application to the study of plant cell wall lignification. Chem Commun (Camb). 2021 Jan 11;57(3):404. doi: 10.1039/d0cc90541k. Epub 2021 Jan 4. Erratum for: Chem Commun (Camb). 2021 Jan 14;57(3):387-390. PMID: 33393953.
4: Sun X, Song H, Wen J, Hu Y, Zhang M, Li W, Ding Z. Research on serum metabolomics of ovariectomized rats and intervention effect of Cuscuta chinensis on metabolic pattern. J Pharm Biomed Anal. 2021 Feb 20;195:113847. doi: 10.1016/j.jpba.2020.113847. Epub 2020 Dec 13. PMID: 33358618.
5: Simon C , Lion C , Ahouari H , Vezin H , Hawkins S , Biot C . EPR imaging of sinapyl alcohol and its application to the study of plant cell wall lignification. Chem Commun (Camb). 2021 Jan 14;57(3):387-390. doi: 10.1039/d0cc05218c. Erratum in: Chem Commun (Camb). 2021 Jan 4;: PMID: 33326527.
6: Abdel-Aty AM, Salama WH, El-Badry MO, Salah HA, Barakat AZ, Fahmy AS, Mohamed SA. Purification and characterization of peroxidases from garden cress sprouts and their roles in lignification and removal of phenol and p-chlorophenol. J Food Biochem. 2021 Jan;45(1):e13526. doi: 10.1111/jfbc.13526. Epub 2020 Nov 2. PMID: 33140461.
7: Ding Z, Fu L, Tie W, Yan Y, Wu C, Dai J, Zhang J, Hu W. Highly dynamic, coordinated, and stage-specific profiles are revealed by a multi-omics integrative analysis during tuberous root development in cassava. J Exp Bot. 2020 Dec 31;71(22):7003-7017. doi: 10.1093/jxb/eraa369. PMID: 32777039.
8: Kawabata T, Tanaka Y, Horinishi A, Mori M, Hosoda A, Yamamoto N, Mitani T. Subcritical Methanol Extraction of the Stone of Japanese Apricot Prunus mume Sieb. et Zucc. Biomolecules. 2020 Jul 15;10(7):1047. doi: 10.3390/biom10071047. PMID: 32679686; PMCID: PMC7407280.
9: García-Ulloa A, Sanjurjo L, Cimini S, Encina A, Martínez-Rubio R, Bouza R, Barral L, Estévez-Pérez G, Novo-Uzal E, De Gara L, Pomar F. Overexpression of ZePrx in Nicotiana tabacum Affects Lignin Biosynthesis Without Altering Redox Homeostasis. Front Plant Sci. 2020 Jun 26;11:900. doi: 10.3389/fpls.2020.00900. PMID: 32676088; PMCID: PMC7333733.
10: Chaubey A, Dubey AK. Chemistry and Antioxidant Potential of Phytoconstituents from Aegle Marmelos Fruit-Shell. Curr Drug Metab. 2020;21(7):525-533. doi: 10.2174/1389200221666200711161056. PMID: 32651962.
11: Osorio-González CS, Hegde K, Brar SK, Vezina P, Gilbert D, Avalos-Ramírez A. Pulsed-ozonolysis assisted oxidative treatment of forestry biomass for lignin fractionation. Bioresour Technol. 2020 Oct;313:123638. doi: 10.1016/j.biortech.2020.123638. Epub 2020 Jun 5. PMID: 32534757.
12: Antúnez-Argüelles E, Herrera-Bulnes M, Torres-Ariño A, Mirón-Enríquez C, Soriano-García M, Robles-Gómez E. Enzymatic-assisted polymerization of the lignin obtained from a macroalgae consortium, using an extracellular laccase- like enzyme (Tg-laccase) from Tetraselmis gracilis. J Environ Sci Health A Tox Hazard Subst Environ Eng. 2020;55(6):739-747. doi: 10.1080/10934529.2020.1738171. Epub 2020 Mar 17. PMID: 32181694.
13: Xie T, Liu Z, Wang G. Structural basis for monolignol oxidation by a maize laccase. Nat Plants. 2020 Mar;6(3):231-237. doi: 10.1038/s41477-020-0595-5. Epub 2020 Mar 2. PMID: 32123349.
14: Wang S, Innocent MT, Wang Q, Xiang H, Tang J, Zhu M. Kraft lignin-based piezoresistive sensors: Effect of chemical structure on the microstructure of ultrathin carbon fibers. Int J Biol Macromol. 2020 May 15;151:730-739. doi: 10.1016/j.ijbiomac.2020.02.225. Epub 2020 Feb 20. PMID: 32088235.
15: Yamashita A, Kishimoto T, Hamada M, Nakajima N, Urabe D. Biomimetic Oxidation of Monolignol Acetate and p-Coumarate by Silver Oxide in 1,4-Dioxane. J Agric Food Chem. 2020 Feb 19;68(7):2124-2131. doi: 10.1021/acs.jafc.9b07682. Epub 2020 Feb 10. PMID: 31985223.
16: Qin G, Liu C, Li J, Qi Y, Gao Z, Zhang X, Yi X, Pan H, Ming R, Xu Y. Diversity of metabolite accumulation patterns in inner and outer seed coats of pomegranate: exploring their relationship with genetic mechanisms of seed coat development. Hortic Res. 2020 Jan 7;7:10. doi: 10.1038/s41438-019-0233-4. PMID: 31934341; PMCID: PMC6946660.
17: He F, Machemer-Noonan K, Golfier P, Unda F, Dechert J, Zhang W, Hoffmann N, Samuels L, Mansfield SD, Rausch T, Wolf S. The in vivo impact of MsLAC1, a Miscanthus laccase isoform, on lignification and lignin composition contrasts with its in vitro substrate preference. BMC Plant Biol. 2019 Dec 12;19(1):552. doi: 10.1186/s12870-019-2174-3. PMID: 31830911; PMCID: PMC6909574.
18: Yang Y, Yoo CG, Rottmann W, Winkeler KA, Collins CM, Gunter LE, Jawdy SS, Yang X, Pu Y, Ragauskas AJ, Tuskan GA, Chen JG. PdWND3A, a wood-associated NAC domain-containing protein, affects lignin biosynthesis and composition in Populus. BMC Plant Biol. 2019 Nov 11;19(1):486. doi: 10.1186/s12870-019-2111-5. PMID: 31711424; PMCID: PMC6849256.
19: Lam PY, Tobimatsu Y, Matsumoto N, Suzuki S, Lan W, Takeda Y, Yamamura M, Sakamoto M, Ralph J, Lo C, Umezawa T. OsCAldOMT1 is a bifunctional O-methyltransferase involved in the biosynthesis of tricin-lignins in rice cell walls. Sci Rep. 2019 Aug 12;9(1):11597. doi: 10.1038/s41598-019-47957-0. PMID: 31406182; PMCID: PMC6690965.
20: Aoki D, Okumura W, Akita T, Matsushita Y, Yoshida M, Sano Y, Fukushima K. Microscopic distribution of syringin in freeze-fixed Syringa vulgaris stems. Plant Direct. 2019 Aug 2;3(8):e00155. doi: 10.1002/pld3.155. PMID: 31388649; PMCID: PMC6676449.