6627-88-9

Basic information

• Product Name: 4-ALLYL-2,6-DIMETHOXYPHENOL
• Synonyms: FEMA 3655;4-ALLYLSYRINGOL;4-ALLYL-2,6-DIMETHOXYPHENOL;TIMTEC-BB SBB003607;2,6-dimethoxy-4-(2-propenyl)-pheno;2,6-Dimethoxy-4-(2-propenyl)phenol;2,6-Dimethoxy-4-allylphenol;4-(2-Propenyl)-2,6-dimethoxyphenol (4-allylsyringol)
• CAS NO: 6627-88-9
• Molecular Formula: C₁₁H₁₄O₃
• Molecular Weight: 194.23
• EINECS: 229-600-2
• Product Categories: Aromatic Phenols;Organic Building Blocks;Oxygen Compounds;Phenols;A-B;Alphabetical Listings;Flavors and Fragrances;Building Blocks;C9 to C20+;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 6627-88-9.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 168-169 °C11 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: clear yellow to orange liquid
• Density: 1.092 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00059mmHg at 25°C
• Refractive Index: n20/D 1.548(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 10.31±0.23(Predicted)
• Water Solubility: Soluble in fats. Insoluble in water.
• CAS DataBase Reference: 4-ALLYL-2,6-DIMETHOXYPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ALLYL-2,6-DIMETHOXYPHENOL(6627-88-9)
• EPA Substance Registry System: 4-ALLYL-2,6-DIMETHOXYPHENOL(6627-88-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-37/39-36/37
• WGK Germany: 3
• Hazardous Substances Data: 6627-88-9(Hazardous Substances Data)

Usage

Identification

▼▲ CAS.No.:? 6627-88-9? FL.No.:? 4.051 FEMA.No.:? 3655 NAS.No.:? 3655 CoE.No.:? 11214 EINECS.No.:? 229-600-2? JECFA.No.:? 726

Description

A clear liquid with a roasted, burnt, meaty, bacon aroma. It is used as a flavoring agent or adjuvant.

Regulatory Status

CoE: n/a FDA: n/a FDA (other): n/a JECFA: ADI: Acceptable. No safety concern when used at current levels as a flavoring agent (2000).

Usage

Reported uses (ppm): (FEMA, 1994) ▼▲ Food Category? Usual? Max.? Cheese? 0.1 0.5 Condiments, relishes? 1 5 Gravies? 0.1 0.5 Meat products? 0.1 0.5 Poultry? 0.05 0.2 Seasoning, flavorings? 1 5 Snack foods? 0.1 0.5 Soups? 0.05 0.2

Natural occurrence

Reported found in nutmeg, smoked pork belly, smoked sausage, natural smoked flavor banana, sherry and red wine.

Chemical Properties

Different sources of media describe the Chemical Properties of 6627-88-9 differently. You can refer to the following data:
1. CLEAR YELLOW TO ORANGE LIQUID
2. A clear liquid with a roasted, burnt, meaty, bacon aroma. It is used as a flavoring agent or adjuvant

Occurrence

Reported found in nutmeg, smoked pork belly, smoked sausage, natural smoked flavor banana, sherry and red wine

Uses

4-Allyl-2,6-dimethoxyphenol is used as a flavoring agent or adjuvant. Also used to produce 2,6-Dimethoxy-4-propyl-phenol.

Aroma threshold values

Detection at 1.2 ppm

Taste threshold values

Taste characteristics at 20 ppm: meaty, phenolic, smoky and bacony, with creamy, vanilla nuances

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 1746, 1948 DOI: 10.1021/ja01185a020

InChI:InChI=1/C11H14O3/c1-4-5-8-6-9(13-2)11(12)10(7-8)14-3/h4,6-7,12H,1,5H2,2-3H3

Upstream product

• 623-11-0 1-methyl-4-nitrosobenzene 
• 1147-85-9 methyl 4-(allyloxy)-3,5-dimethoxybenzoate 
• 5438-54-0 1,3-dimethoxy-2-[(prop-2-en-1-yl)oxy]benzene 
• 121-69-7 N,N-dimethyl-aniline 
• 884-35-5 methyl syringate 
• 58623-87-3 2,6-dimethoxy-4-(2-propenylidene)-2,5-cyclohexadien-1-one 
• 118-41-2 Eudesmic acid 
• 530-57-4 3,5-dimethoxy-4-hydroxybenzoic acid 
• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 634-36-6 1,2,3-trimethoxybenzene 
• 106-95-6 allyl bromide 
• 1466-01-9 4-(2-propenoxy)-3,5-dimethoxybenzoic acid 
• 38451-63-7 4,4a-dihydro-1,5,5,6,9,9-hexamethoxy-3,8a-bis(2-propenyl)-1,4-ethanonaphthalene-6,10(4H)-dione 

Downstream Products

• 41535-97-1 1-(3',4'-dimethoxyphenyl)-2-(2,6-dimethoxy-4-allyl-phenoxy) propan-1-one 
• 89706-47-8 1-(4-hydroxy-3,5-dimethoxyphenyl)-2-<2,6-dimethoxy-4-(1-propenyl)phenoxy>propane 
• 66463-74-9 2,6-Dimethoxy-4-(1-methoxy-allyl)-phenol 
• 66463-76-1 4-[2-(4-Allyl-2,6-dimethoxy-phenoxy)-1,3-dimethoxy-propyl]-2,6-dimethoxy-phenol 
• 94930-82-2 2,6-Dimethoxy-4-(3-methoxy-trans-propenyl)-phenol 
• 20675-95-0 (E)-2,6,-dimethoxy-4-(prop-1-en-1-yl)phenol 
• 58623-87-3 2,6-dimethoxy-4-(2-propenylidene)-2,5-cyclohexadien-1-one 
• 20675-96-1 trans-sinapyl alcohol 
• 38451-63-7 4,4a-dihydro-1,5,5,6,9,9-hexamethoxy-3,8a-bis(2-propenyl)-1,4-ethanonaphthalene-6,10(4H)-dione 
• 638990-29-1 (S)-3-(3,4,5-trimethoxyphenyl)-1,2-propanediol 
• 638990-30-4 (R)-3-(3,4,5-trimethoxyphenyl)-1,2-propanediol 
• 638168-43-1 (S)-3-(3,4,5-trimethoxyphenyl)-1-O-benzoyl-1,2-propanediol 
• 638168-45-3 (R)-3-(3,4,5-trimethoxyphenyl)-1-O-benzoyl-1,2-propanediol 
• 638168-46-4 (S)-3-(3,4,5-trimethoxyphenyl)-1-O-benzoyl-2-O-(4-allyl-2,6-dimethoxyphenyl)-1,2-propanediol 

Relevant articles and documents

Efficient demethylation of aromatic methyl ethers with HCl in water

A green, efficient and cheap demethylation reaction of aromatic methyl ethers with mineral acid (HCl or H2SO4) as a catalyst in high temperature pressurized water provided the corresponding aromatic alcohols (phenols, catechols, pyrogallols) in high yield. 4-Propylguaiacol was chosen as a model, given the various applications of the 4-propylcatechol reaction product. This demethylation reaction could be easily scaled and biorenewable 4-propylguaiacol from wood and clove oil could also be applied as a feedstock. Greenness of the developed methodversusstate-of-the-art demethylation reactions was assessed by performing a quantitative and qualitative Green Metrics analysis. Versatility of the method was shown on a variety of aromatic methyl ethers containing (biorenewable) substrates, yielding up to 99% of the corresponding aromatic alcohols, in most cases just requiring simple extraction as work-up.

Investigating the microwave-accelerated Claisen rearrangement of allyl aryl ethers: Scope of the catalysts, solvents, temperatures, and substrates

The microwave-accelerated Claisen rearrangement of allyl aryl ethers was investigated, in order to gain insight into the scope of the catalysts, solvents, temperatures, and substrates. Among the catalysts examined, phosphomolybdic acid (PMA) was found to greatly accelerate the reaction in NMP, at temperatures ranging from 220 to 300 °C. This method was found to be useful for preparing several intermediates previously reported in the literature using precious metal catalysts such as Au(I), Ag(I), and Pt(II). Additionally, substrates bearing bromo and nitro groups on the aryl portion required careful tailoring of the reaction conditions to avoid complex product profiles.

Modular synthesis of (E)-cinnamaldehydes directly from allylarenes via a metal-free DDQ-mediated oxidative process

An efficient synthesis of (E)-cinnamaldehydes by a metal-free DDQ-mediated oxidative transformation of allylarenes was developed. The protocol provides a practical method to prepare diverse (E)-cinnamaldehydes with broad functional group tolerance in good to excellent yields, including easy access to natural products randainal and geranyloxy sinapyl aldehyde from plant extracts. Finally, the mechanism of a single-electron transfer process was proposed.