20675-96-1

Basic information

• Product Name: Phenol,4-[(1E)-3-hydroxy-1-propenyl]-2,6-dimethoxy-
• Synonyms: 2-Propen-1-ol,3-(4-hydroxy-3,5-dimethoxyphenyl)-, (E)- (8CI); Phenol,4-(3-hydroxy-1-propenyl)-2,6-dimethoxy-, (E)-; (E)-Sinapyl alcohol; Syringenin;trans-Sinapyl alcohol
• CAS NO: 20675-96-1
• Molecular Formula: C11H14 O4
• Molecular Weight: 210.23
• Mol File: 20675-96-1.mol
• Article Data: 31

Chemical Properties

• CAS DataBase Reference: Phenol,4-[(1E)-3-hydroxy-1-propenyl]-2,6-dimethoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol,4-[(1E)-3-hydroxy-1-propenyl]-2,6-dimethoxy-(20675-96-1)
• EPA Substance Registry System: Phenol,4-[(1E)-3-hydroxy-1-propenyl]-2,6-dimethoxy-(20675-96-1)

Safety Data

• Hazardous Substances Data: 20675-96-1(Hazardous Substances Data)

Usage

General Description

Phenol, 4-[(1E)-3-hydroxy-1-propenyl]-2,6-dimethoxy- is a chemical compound with the molecular formula C12H16O4. It is a type of phenol with a hydroxypropenyl group and two methoxy groups attached to the benzene ring. Phenol,4-[(1E)-3-hydroxy-1-propenyl]-2,6-dimethoxy- is commonly found in various plants and is known for its antioxidant and antimicrobial properties. It has been studied for its potential use in pharmaceuticals and as a natural preservative in food and cosmetics. Research also suggests that it may have potential health benefits, such as anti-inflammatory and anti-cancer properties.

Upstream product

• 118-34-3 syringin 
• 1782-47-4 5-hydroxyconiferyl alcohol 
• 14031-35-7 S-Adenosyl-L-methionine 
• 134-96-3 syringic aldehyde 
• 530-59-6 sinapinic acid 
• 106852-80-6 4-(t-butyldimethylsilyloxy)-3,5-dimethoxybenzaldehyde 
• 136196-47-9 3-hydroxy-1-(3,5-dimethoxy-4-hydroxyphenyl)-propan-1-one 
• 41628-47-1 ethyl (2E)-3-[4-hydroxy-3,5-bis(methyloxy)phenyl]-2-propenoate 
• 58623-87-3 2,6-dimethoxy-4-(2-propenylidene)-2,5-cyclohexadien-1-one 
• 71686-40-3 (E)-2,6-dimethoxy-4-(3-oxoprop-1-en-1-yl)phenyl acetate 
• 53669-33-3 4-acetoxy-3,5-dimethoxybenzaldehyde 
• 90985-68-5 (E)-4-acetoxy-3,5-dimethoxycinnamic acid 
• 530-59-6 trans-3,5-dimethoxy-4-hydroxycinnamic acid 
• 4206-58-0 (E)-sinapinaldehyde 

Downstream Products

• 487-35-4 (+/-)-syringaresinol 
• 116718-15-1 3'-O-methylxanthocercin A 
• 887914-26-3 (1R,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-(4-((E)-3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy)propane-1,3-diol 
• 203179-64-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((E)-3-hydroxyprop-1-en-1 -yl)-2,6-dimethoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 65109-39-9 4-(2-(2,6-dimethoxyphenoxy)-1-hydroxyethyl)-2,6-dimethoxyphenol 
• 6638-05-7 2,6-dimethoxy-4-methylphenol 
• 2478-38-8 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone 
• 15640-40-1 bis(4-hydroxy-2,6-dimethoxyphenyl)methane 
• 20824-45-7 4-hydroxy-3,5-dimethoxyphenethyl alcohol 
• 134-96-3 syringic aldehyde 
• 487-35-4 (+)-syringaresinol 
• 76246-81-6 1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone benzyl ether 

Relevant articles and documents

Highly Selective Syntheses of Coniferyl and Sinapyl Alcohols

(E)-Isomers of coniferyl and sinapyl alcohols were readily and cleanly prepared in excellent yields from comercially available coniferaldehyde and sinapaldehyde by sodium triacetoxyborohydride reduction in ethyl acetate.No 1,4-reduction products, always produced in prior methods, could be detected. - Keywords: coniferyl alcohol; sinapyl alcohol; monolignol; lignin; triacetoxyborohydride; dihydroconiferyl alcohol; coniferaldehyde; sinapaldehyde; regiospecific reduction

Improved Preparation of Coniferyl and Sinapyl Alcohols

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First total syntheses of two natural glycosides

Isosyringinoside (1) and 3-(O-β-D-glucopyranosyl)-α-(O-β-D-glucopyranosyl)-4-hydroxy phenylethanol (2), the natural bioactive compounds contained unique structures, were first totally synthesized using easily available materials in short convenient routes with overall yields of 20.2% and 27.0%, respectively. An efficient total synthesis of 1 was developed in six steps, which contained two key steps of highly regioselective glycosylation without any selective protection steps. The seven-step synthesis of 2 involved two steps of regioselective glycosylations using BF3–O(C2H5)2 and TMSOTf as catalysts, respectively.

Total Syntheses and Anti-inflammatory Activities of Syringin and Its Natural Analogues

Syringin (1), a natural bioactive glucoside isolated from the root of Acanthopanax senticosus (Rupr. Maxim.) Harms, possesses significant anti-inflammatory activity. In this study, we have accomplished the total syntheses of syringin (1), along with its natural analogues 2-12, from a common starting material, syringaldehyde (13), in 4-8 steps with an overall yields of 11.8-61.3%. The anti-inflammatory activities of these compounds were determined against NO production in the LPS-stimulated RAW264.7 cells. Among them, compounds 1-5, 7, and 9 exhibited different levels of anti-inflammatory activity.