884-35-5

Basic information

• Product Name: Methyl syringate
• Synonyms: METHYL 3,5-DIMETHOXY-4-HYDROXYBENZOATE;METHYL-4-HYDROXY-3,5-DIMETHOXYBENZOATE;METHYL SYRINGATE;3,5-DIMETHOXY-4-HYDROXYBENZOIC ACID METHYL ESTER;RARECHEM AL BF 0102;methyl syringoate;Syringic acid monomethyl ester;4-Hydroxy-3,5-Dimethoxybenzoic Acid Methyl Ester
• CAS NO: 884-35-5
• Molecular Formula: C₁₀H₁₂O₅
• Molecular Weight: 212.2
• EINECS: 429-050-5
• Product Categories: Aromatic Esters;Acids & Esters;Anisoles, Alkyloxy Compounds & Phenylacetates;Phenols;Pharmaceutical Intermediate
• Mol File: 884-35-5.mol
• Article Data: 28

Chemical Properties

• Melting Point: 103-107 °C
• Boiling Point: 312.03°C (rough estimate)
• Flash Point: 132.4 °C
• Appearance: beige powder
• Density: 1.3006 (rough estimate)
• Vapor Pressure: 4.54E-05mmHg at 25°C
• Refractive Index: 1.5140 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 8.38±0.23(Predicted)
• Water Solubility: Soluble in alcohol, ether, slightly soluble in water.
• BRN: 2217524
• CAS DataBase Reference: Methyl syringate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl syringate(884-35-5)
• EPA Substance Registry System: Methyl syringate(884-35-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-60-37
• Hazardous Substances Data: 884-35-5(Hazardous Substances Data)

Usage

Chemical Properties

BEIGE POWDER

Uses

Methyl Syringate is used in studies of volatile compound and sensorial characterization of red wine aged in cherry, chestnut, false acacia, ash and oak wood barrels

Definition

ChEBI: A benzoate ester obtained by the formal condensation of carboxy group of syringic acid with methanol.

InChI:InChI=1/C10H12O5/c1-13-7-4-6(10(12)15-3)5-8(14-2)9(7)11/h4-5,11H,1-3H3

Synthetic route

methanol (67-56-1) + 3,5-dimethoxy-4-hydroxybenzoic acid (530-57-4) → methyl syringate (884-35-5)

Conditions	Yield
With sulfuric acid for 6h; Reflux;	100%
With sulfuric acid for 3h; Reflux;	96%
With thionyl chloride at 50℃; for 18h;	96%

3,4,5-trimethoxybenzoic acid methyl ester (1916-07-0) → methyl syringate (884-35-5)

Conditions	Yield
With iodine; magnesium In diethyl ether; dichloromethane at 80℃; for 1h;	100%
Stage #1: 3,4,5-trimethoxybenzoic acid methyl ester With aluminum (III) chloride In dichloromethane at 20℃; Stage #2: With hydrogenchloride; water In dichloromethane; chloroform	98%
Stage #1: 3,4,5-trimethoxybenzoic acid methyl ester With aluminum (III) chloride In dichloromethane at 20℃; Stage #2: With hydrogenchloride In chloroform	98%

methanol (67-56-1) + 4-methyl-3,5-dimethoxybenzoic acid (61040-81-1) → methyl syringate (884-35-5)

Conditions	Yield
With thionyl chloride at 0℃; Reflux;	95%

methyl 4-benzyloxy-3,5-dimethoxybenzoate (27065-65-2) → methyl syringate (884-35-5)

Conditions	Yield
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In methanol at 0℃;	90%
With palladium on activated charcoal; ethanol Hydrogenation;
With hydrogen; palladium on activated charcoal

methyl 4-(allyloxy)-3,5-dimethoxybenzoate (1147-85-9) → methyl syringate (884-35-5)

Conditions	Yield
With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 2h; Ambient temperature;	90%
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In methanol at 0℃;	88%

methyl 3,5-dimethoxy-4-methoxymethoxybenzoate → 3,5-dimethoxy-4-hydroxybenzoic acid (530-57-4) + methyl syringate (884-35-5)

Conditions	Yield
With ethylene glycol at 120℃; for 1h;	A 10% B 78%

diazomethane (186581-53-3, 908094-01-9) + 6-O-syringyl-8-O-acetyl shanzhiside methyl ester (86450-76-2) → methyl syringate (884-35-5) + shanzhiside methyl ester (64421-28-9)

Conditions	Yield
With sodium hydroxide 1.) methanol, room temperature, 4 d; Multistep reaction;

methanol (67-56-1) + 6-O-syringyl-8-O-acetyl shanzhiside methyl ester (86450-76-2) → methyl syringate (884-35-5)

Conditions	Yield
With sodium hydroxide for 96h; Ambient temperature;

Methyl syringate 4-O-α-L-rhamnopyranoside (130774-07-1) → methyl syringate (884-35-5)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; water for 1h; Heating;	15 mg

6-O-syringyl-8-O-acetyl shanzhiside methyl ester (86450-76-2) → methyl syringate (884-35-5) + shanzhiside (29836-27-9)

Conditions	Yield
With sodium hydroxide In methanol Ambient temperature;

hydrogenchloride (7647-01-0) + methanol (67-56-1) + O-acetylsyringic acid (6318-20-3) → methyl syringate (884-35-5)

2-Methoxyhydroquinone 4-O-<6-O-(4-O-α-L-rhamnopyranosyl)-syringyl>-β-D-glucopyranoside (136112-50-0) → methyl syringate (884-35-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 59 mg / K2CO3 / Ambient temperature 2: 15 mg / aq. HCl / dioxane; H2O / 1 h / Heating View Scheme

Coniferin 6'-O-(4-O-α-L-rhamnopyranosyl)-syringate → methyl syringate (884-35-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 52 mg / K2CO3 / 0.5 h / Ambient temperature 2: 15 mg / aq. HCl / dioxane; H2O / 1 h / Heating View Scheme

Eudesmic acid (118-41-2) → methyl syringate (884-35-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated hydrochloric acid / im geschlossenen Rohr 2: HCl View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid / 24 h / Reflux; Inert atmosphere 2: boron trichloride / dichloromethane / 30 h / -10 - 20 °C / Inert atmosphere View Scheme

Upstream product

• 67-56-1 methanol 
• 530-57-4 3,5-dimethoxy-4-hydroxybenzoic acid 
• 1916-07-0 3,4,5-trimethoxybenzoic acid methyl ester 
• 1147-85-9 methyl 4-(allyloxy)-3,5-dimethoxybenzoate 
• 74-83-9 methyl bromide 
• 61040-81-1 4-methyl-3,5-dimethoxybenzoic acid 
• 9005-53-2 lignin 
• 118-41-2 Eudesmic acid 
• 136112-50-0 2-Methoxyhydroquinone 4-O-<6-O-(4-O-α-L-rhamnopyranosyl)-syringyl>-β-D-glucopyranoside 
• 7647-01-0 hydrogenchloride 
• 6318-20-3 O-acetylsyringic acid 
• 86450-76-2 6-O-syringyl-8-O-acetyl shanzhiside methyl ester 
• 130774-07-1 Methyl syringate 4-O-α-L-rhamnopyranoside 
• 186581-53-3 diazomethane 

Downstream Products

• 182183-08-0 3,5-dimethoxy-4-phenoxy-benzoic acid methyl ester 
• 17297-22-2 (4-Hydroxy-3,5-dimethoxy-phenyl)-diphenyl-methanol 
• 890-47-1 methyl 4-acetoxy-3,5-dimethoxybenzoate 
• 99463-12-4 methyl 4-<(5'-formylfuran-2'-yl)methoxy>-3,5-dimethoxybenzoate 
• 1916-07-0 3,4,5-trimethoxybenzoic acid methyl ester 
• 1025835-48-6 4-Decyloxy-3,5-dimethoxy-benzoic acid methyl ester 
• 27065-65-2 methyl 4-benzyloxy-3,5-dimethoxybenzoate 
• 260418-39-1 4-hydroxy-3,5-dimethoxy-2-nitro-benzoic acid methyl ester 
• 2478-38-8 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone 
• 30835-78-0 ethyl 3-(4-benzyloxy-3,5-dimethoxyphenyl)-3-oxopropionate 
• 860579-04-0 2-(4-benzyloxy-3,5-dimethoxy-benzoyl)-3-oxo-butyric acid ethyl ester 
• 3086-85-9 4-benzyloxy-3,5-dimethoxy-benzoic acid amide 
• 76246-81-6 1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone benzyl ether 
• 860742-50-3 1-(4-benzyloxy-3,5-dimethoxy-phenyl)-2-diazo-ethanone 

Relevant articles and documents

CHRYSOPHAENTIN ANALOGS AND USE THEREOF

Provided are 9-dechlorochrysophaentin analog compounds and the synthesis process thereof. The disclosed compound have remarkable antimicrobial activitivies that are comparable to, or even more potent than, the natural product chrysophaentin A. Also provided are method of inhibiting bacterial growth or treating bacterial infection by administering an effective amount of the disclosed compounds.

Antifungal activity of cinnamic acid and benzoic acid esters against Candida albicans strains

Candida albicans is an important opportunistic fungal pathogen capable of provoking infection in humans. In the present study, we evaluated the antifungal effect of 23 ester derivatives of the cinnamic and benzoic acids against 3 C. albicans strains (ATCC-76645, LM-106 and LM-23), as well as discuss their Structure–Activity Relationship (SAR). The antifungal assay results revealed that the screened compounds exhibited different levels of activity depending on structural variation. Among the ester analogues, methyl caffeate (5) and methyl 2-nitrocinnamate (10) were the analogues that presented the best antifungal effect against all C. albicans strains, presenting the same MIC values (MIC?=?128?μg/mL), followed by methyl biphenyl-2-carboxylate (21) (MIC?=?128, 128 and 256?μg/mL for C. albicans LM-106, LM-23, and ATCC-76645, respectively). Our results suggest that certain molecular characteristics are important for the antifungal action.

Composition FOR PREVENTING ALOPECIA AND ACTIVATING HAIR GROWTH

The present invention provides a hair growth promoter comprising as an active ingredient, a compound having a chemical structure of general formula (1) or a pharmacologically acceptable salt thereof. In the general formula (1): R_1 is a saturated or unsaturated straight chain or branched C1-C10 alkyl group or hydroxy alkyl group; R_2 is hydrogen or a saturated or unsaturated straight chain or branched C1-C10 alkoxy or hydroxy alkoxy; X is hydrogen, hydroxy, or a saturated or unsaturated straight chain or branched C1-C10 alkyl group, alkoxy or hydroxyl alkoxy; R_3 and R_4 are each independently selected from R_5, hydrogen, aldehyde, and a saturated or unsaturated straight chain or branched alkyl, alkoxy, or hydroxy alkoxy; R_5 has a structure of # AAA #; R_6 is selected from hydrogen, and a saturated or unsaturated straight chain or branched C1-C10 alkyl, alkoxy, or hydroxy alkoxy; and one of R_3 and R_4 is hydrogen.COPYRIGHT KIPO 2017