32811-40-8

Basic information

• Product Name: Coniferyl alcohol
• Synonyms: (E)-Coniferol;trans-3-(4-Hydroxy-3-methoxyphenyl)-2-propen-1-ol
• CAS NO: 32811-40-8
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.20048
• Mol File: 32811-40-8.mol

Chemical Properties

• Melting Point: 170-171 °C
• Boiling Point: 332.2±0.0 °C(Predicted)
• Appearance: /
• Density: 1.198±0.06 g/cm3(Predicted)
• PKA: 10.04±0.31(Predicted)
• CAS DataBase Reference: Coniferyl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: Coniferyl alcohol(32811-40-8)
• EPA Substance Registry System: Coniferyl alcohol(32811-40-8)

Safety Data

• Hazardous Substances Data: 32811-40-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
Coniferyl alcohol is used as a precursor in the chemical industry for the synthesis of various lignin-based materials and products. Its ability to be converted into lignin makes it a valuable compound for the development of bio-based materials and chemicals.
Used in Pharmaceutical Industry:
Coniferyl alcohol is used as a starting material for the synthesis of various pharmaceutical compounds, including drugs with potential applications in the treatment of various diseases. Its unique chemical structure allows for the development of novel therapeutic agents.
Used in Environmental Applications:
Due to its presence in wood smoke and the ambient atmosphere, coniferyl alcohol can be used as a marker for the study of air pollution and the impact of biomass burning on the environment. Understanding its role in these processes can help in the development of strategies to reduce air pollution and improve air quality.
Used in Plant Biology Research:
Coniferyl alcohol is used as a research tool in plant biology to study the process of lignin biosynthesis and its role in plant growth and development. This research can lead to a better understanding of plant cell wall structure and function, as well as the potential for genetic manipulation to improve plant properties for various applications, such as biomass production for bioenergy.

Upstream product

• 37791-78-9 (2E)-3-(4-O-acetyl-3-methoxyphenyl)prop-2-en-1-yl acetate 
• 7382-59-4 guaiacylglycerol-β-guaiacyl ether 
• 458-36-6 trans-coniferyl aldehyde 
• 97-53-0 4-allylguaiacol 
• 74953-23-4 trans-3-(4-acetoxy-3-methoxyphenyl)-2-propenyl bromide 
• 124151-33-3 coniferin 
• 28028-62-8 ethyl ferulate 
• 5932-68-3 (E)-2-methoxy-4-(1-propenyl)phenol 
• 121-33-5 vanillin 
• 50906-12-2 4-acetoxy-3-methoxycinnamoyl chloride 
• 2596-47-6 (E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid 
• 129664-76-2 2-methoxy-4-(2-propenylidene)-2,5-cyclohexadien-1-one, Z-isomer 
• 5912-87-8 (E)-1-(4-acetoxy-3-methoxyphenyl)-1-propene 
• 93-28-7 eugenol acetate 

Downstream Products

• 38153-27-4 (2E)-3-(4-O-benzyloxy-3-methoxyphenyl)prop-2-en-1-ol 
• 77550-11-9 4-cis,8-cis-bis(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo<3.3.0>octane-2,6-dione 
• 3810-34-2 4-endo-8-exo-bis-(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo<3.3.0>octan-2-one 
• 3810-34-2 4-cis,8-cis-bis(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo<3.3.0>octan-2-one 
• 487-36-5 (+/-)-pinoresinol 
• 37791-78-9 (2E)-3-(4-O-acetyl-3-methoxyphenyl)prop-2-en-1-yl acetate 
• 1137653-03-2 cleomiscosin B 
• 97465-82-2 (2S,3R)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-5-[(E)-3-hydroxy-1-propenyl]-3-hydroxymethyl-7-methoxybenzo[b]furan 
• 155836-29-6 (2R,3S)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-5-[(1E)-3-hydroxyprop-1-en-1-yl]-7-methoxybenzofuran-3-methanol 
• 3688-23-1 (-)-secoisolariciresinol 
• 145265-02-7 (-)-secoisolariciresinol 

Relevant articles and documents

Consolidated production of coniferol and other high-value aromatic alcohols directly from lignocellulosic biomass

Sustainable production of fine chemicals and biofuels from renewable biomass offers a potential alternative to the continued use of finite geological oil reserves. However, in order to compete with current petrochemical refinery processes, alternative biorefinery processes must overcome significant costs and productivity barriers. Herein, we demonstrate the biocatalytic production of the versatile chemical building block, coniferol, for the first time, directly from lignocellulosic biomass. Following the biocatalytic treatment of lignocellulose to release and convert ferulic acid with feruloyl esterase (XynZ), carboxylic acid reductase (CAR) and aldo-keto reductase (AKR), this whole cell catalytic cascade not only achieved equivalent release of ferulic acid from lignocellulose compared to alkaline hydrolysis, but also displayed efficient conversion of ferulic acid to coniferol. This system represents a consolidated biodegradation-biotransformation strategy for the production of high value fine chemicals from waste plant biomass, offering the potential to minimize environmental waste and add value to agro-industrial residues.

Solid phase synthesis of cis-coniferyl alcohol

Synthesis of cis-coniferyl alcohol (4-hydroxy-5-methoxy- cinnamyl alcohol), using support on Wang's resin is described.

Cinnamyl alcohols and methyl esters of fatty acids from Wedelia prostrata callus cultures

Two methyl esters of fatty acids, namely octadecanoic acid methyl ester (methyl stearate) (1) and hexadecanoic acid methyl ester (methyl palmitate) (2), in addition to four cinnamyl alcohol derivatives, sinapyl alcohol (3), coniferyl alcohol (4), p-coumaryl alcohol (5) and coniferyl alcohol 4-O-glucoside (coniferin) (6), were isolated from callus cultures of Wedelia prostrata. The structure of coniferin was established by spectroscopic and chemical methods, while the other compounds were identified by gas chromatography-mass spectrometry and thin layer chromatography in comparison with standards.

Microbial synthesis of coniferyl alcohol by the fungus Byssochlamys fulva V107

Coniferyl alcohol (123 mM=21.9 g/1) was synthesized from eugenol with a yield of 94.6% in a 36 h fed-batch bioconversion using resting cells of the fungus Byssochlamys fulva V107.

Electrochemical Dimerization of Phenylpropenoids and the Surprising Antioxidant Activity of the Resultant Quinone Methide Dimers

A simple method for the dimerization of phenylpropenoid derivatives is reported. It leverages electrochemical oxidation of p-unsaturated phenols to access the dimeric materials in a biomimetic fashion. The mild nature of the transformation provides excellent functional group tolerance, resulting in a unified approach for the synthesis of a range of natural products and related analogues with excellent regiocontrol. The operational simplicity of the method allows for greater efficiency in the synthesis of complex natural products. Interestingly, the quinone methide dimer intermediates are potent radical-trapping antioxidants; more so than the phenols from which they are derived—or transformed to—despite the fact that they do not possess a labile H-atom for transfer to the peroxyl radicals that propagate autoxidation.

Microwave-Assisted Synthesis of Phenylpropanoids and Coumarins: Total Synthesis of Osthol

Herein we describe a one-pot microwave-assisted method for the synthesis of cinnamic acid and coumarin derivatives. The synthesis begins with an aldehyde synthon, and the chosen reaction conditions determine whether a cinnamic acid or coumarin derivative is formed. A regioselective Claisen rearrangement was also efficiently incorporated into the synthetic sequence to further increase the complexity of the product. Notably, this approach provides high product yields and selectivities without the need of a phenol protecting group.

Anti selective glycolate aldol reactions of (: S)-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one: application towards the asymmetric synthesis of 8-4′-oxyneolignans

The anti selective glycolate aldol reactions of (S)-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one auxiliary have been standardized with high yields and excellent diastereoselectivities on various substituted aryl, allyl and alkyl aldehydes. The optimized reaction conditions were employed for the stereoselective synthesis of oxyneolignans.

Asymmetric Organocatalytic Stepwise [2+2] Entry to Tetra-Substituted Heterodimeric and Homochiral Cyclobutanes

An asymmetric synthesis of tetra-substituted cyclobutanes involving an organocatalytic, stepwise [2+2]-cycloaddition is described. The secondary-amine-catalyzed method allows for the hetero-dimerization of two different cinnamic-acid-derived sub-units, opening a novel one-step assembly to densely functionalized, head-to-tail coupled dimeric cyclobutanes in high enantiomeric excess. A series of selective synthetic interconversions in these sensitive cycloadducts is also described.

MELANIN GENERATION INHIBITOR AND WHITENING AGENT

PROBLEM TO BE SOLVED: To provide a melanin generation inhibitor and a whitening agent that are excellent in whitening effect and also excellent in safety and temporal stability. SOLUTION: The invention provides a melanin generation inhibitor containing a compound represented by formula [1] as an active ingredient, a whitening agent, as well as a melanin generation inhibiting method and a whitening method by applying such agents to the skin. (R1, R2, R4, and R5 are each independently H, a hydroxyl group, an alkyl group of C1-4, or -O-C(=O)R6; R6 is an alkyl group of C1-4; R3 is H, an alkyl group of C1-4, or -C(=O)R7; and R7 is an alkyl group of C1-8.) SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

Synthesis and bioactivity of tripolinolate A from Tripolium vulgare and its analogs

A new coniferol derivative, named as tripolinolate A (1), and 11 known compounds (2-12) were isolated from whole plants of Tripolium vulgare Nees. The structure of this new compound was determined as 4-(2S-methylbutyryl)-9-acetyl-coniferol based on its NMR and HRESIMS spectral analyses. A simple and efficient method was designed to prepare tripolinolate A and its 19 analogs including nine new chemical entities for bioactive assay. Tripolinolate A and its analog 4,9-diacetyl-coniferol were found to be the two most active compounds that significantly inhibited the proliferation of different cancer cell lines with IC50 values ranging from 0.36 to 12.9 μM and induced apoptosis in tumor cells. Structure-activity relationship analysis suggested that the molecular size of acyl moieties at C-4 and C-9 position might have an effect on the activity of this type of coniferol derivatives.