80638-48-8

Basic information

• Product Name: 3-(4-HYDROXY-3-METHOXY-PHENYL)-PROPIONALDEHYDE
• Synonyms: 3-(4-HYDROXY-3-METHOXY-PHENYL)-PROPIONALDEHYDE;Benzenepropanal, 4-hydroxy-3-methoxy-;3-(4-HYDROXY-3-METHOXYPHENYL)PROPANAL;3-(3-Methoxy-4-hydroxyphenyl)propanal;3-Methoxy-4-hydroxybenzenepropanal;3-Methoxy-4-hydroxybenzenepropionaldehyde;4-Hydroxy-3-methoxybenzenepropanal;Dihydroconiferyl aldehyde
• CAS NO: 80638-48-8
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.20048
• EINECS: 279-524-9
• Mol File: 80638-48-8.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 307.8°Cat760mmHg
• Flash Point: 120.7°C
• Appearance: /
• Density: 1.136g/cm³
• Vapor Pressure: 0.000391mmHg at 25°C
• Refractive Index: 1.532
• PKA: 10.04±0.20(Predicted)
• CAS DataBase Reference: 3-(4-HYDROXY-3-METHOXY-PHENYL)-PROPIONALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-HYDROXY-3-METHOXY-PHENYL)-PROPIONALDEHYDE(80638-48-8)
• EPA Substance Registry System: 3-(4-HYDROXY-3-METHOXY-PHENYL)-PROPIONALDEHYDE(80638-48-8)

Safety Data

• Hazardous Substances Data: 80638-48-8(Hazardous Substances Data)

Usage

General Description

3-(4-Hydroxy-3-methoxy-phenyl)-propionaldehyde, also known as "Hydroxyisohexyl 3-cyclohexene carboxaldehyde" or "Lyral," is a synthetic fragrance ingredient commonly used in cosmetics and personal care products. It is often incorporated into perfumes, soaps, lotions, and other scented products due to its distinctive floral, green, and creamy odor profile. However, it has been the subject of some controversy due to its potential to cause skin sensitization and allergic reactions in some individuals, leading to its use being restricted or banned in certain regions. Additionally, it has been classified as a potential respiratory sensitizer, raising concerns about its long-term exposure effects on respiratory health. Due to these potential health risks, some companies have opted to phase out the use of 3-(4-Hydroxy-3-methoxy-phenyl)-propionaldehyde in their products in favor of safer alternatives.

InChI:InChI=1/C10H12O3/c1-13-10-7-8(3-2-6-11)4-5-9(10)12/h4-7,12H,2-3H2,1H3

Upstream product

• 458-36-6 trans-coniferyl aldehyde 
• 2305-13-7 3-Guaiacylpropanol 
• 458-35-5 coniferal alcohol 
• 20649-42-7 coniferaldehyde 
• 28028-62-8 ethyl ferulate 
• 61292-90-8 ethyl 3-(4-hydroxy-3-methoxyphenyl)propanoate 
• 7382-59-4 guaiacylglycerol-β-guaiacyl ether 
• 1135-23-5 3-(4-hydroxy-3-methoxyphenyl)propionic acid 
• 56024-44-3 methyl 3-(4-hydroxy-3-methoxyphenyl)propanoate 
• 4046-02-0 ethyl 4-hydroxy-3-methoxycinnamate 

Downstream Products

• 112798-58-0 γ-(4-Oxy-3-methoxy-phenyl)-propylamin 
• 1612146-71-0 4-(3-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)propyl)benzene-1,2-diol 
• 1612146-60-7 4-(3-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)propyl)-2-methoxyphenol 
• 79067-88-2 (E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-hepten-3-one 
• 960357-30-6 4-(3-hydroxy-3-phenylpropyl)-2-methoxyphenol 
• 39728-80-8 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)butane 
• 1352033-69-2 (E,5S)-1,7-di[4-(benzyloxy)-3-methoxyphenyl]-5-[(4-methoxybenzyl)oxy]-1-hepten-3-one 
• 1352033-60-3 (5S)-7-[4-(benzyloxy)-3-methoxyphenyl]-5-[(4-methoxybenzyl)oxy]-1-hepten-3-one 
• 1352033-66-9 (3S)-5-[4-(benzyloxy)-3-methoxyphenyl]-3-[(4-methoxybenzyl)oxy]pentan-1-ol 
• 1352033-65-8 (4S)-4-[4-(benzyloxy)-3-methoxyphenethyl]-2-(4-methoxyphenyl)-1,3-dioxane 
• 1352033-64-7 (3S)-5-[4-(benzyloxy)-3-methoxyphenyl]pentane-1,3-diol 
• 1352033-63-6 (2S,3S)-3-[4-(benzyloxy)-3-methoxyphenethyl]oxiran-2-ylmethanol 
• 1352033-68-1 C₂₉H₃₄O₅ 

Relevant articles and documents

First enantioselective synthesis of gingesulfonic acids and unequivocal determination of their absolute stereochemistry

Herein we report the first organocatalysed enantioselective synthesis of gingesulfonic acids and shogasulfonic acids via a mild and convenient aminothiourea-catalysed conjugate addition of bisulfite to the olefin moiety of α,β-unsaturated carbonyls - a technology previously reported by us. A series of optically active naturally occurring sulfonic acids are prepared in their natural and unnatural configurations, and their absolute configurations are unequivocally confirmed by single crystal X-ray diffractometry.

The Conjugated Double Bond of Coniferyl Aldehyde Is Essential for Heat Shock Factor 1 Mediated Cytotoprotection

Coniferyl aldehyde (1) is previously reported as a potent inducer of heat shock factor 1 (HSF1). Here, we further examined the active pharmacophore of 1 for activation of HSF1 using the derivatives coniferyl alcohol (2), 4-hydroxy-3-methoxyphenylpropanal (3), and 4-hydroxy-3-methoxyphenylpropanol (4). Both 1 and 2 resulted in increased survival days after a lethal radiation (IR) dose. The decrease in bone marrow (BM) cellularity and Ki67-positive BM cells by IR was also significantly restored by 1 or 2 in mice. These results suggested that the vinyl moiety of 1 and 2 is necessary for inducing HSF1, which may be useful for developing small molecules for cytoprotection of normal cells against damage by cytotoxic drugs and radiation.

Mechanistic investigation of the Zn/Pd/C catalyzed cleavage and hydrodeoxygenation of lignin

While current biorefinery processes use lignin only for its heat value, the conversion of lignin to high value chemicals is an area of increasing interest. Herein we present a detailed mechanistic study of the hydrodeoxygenation (HDO) of lignin by using a synergistic Pd/C and ZnII catalyst through use of both lignin model compounds and lignocellulosic biomass. Spectroscopic data coupled with the study of lignin model compounds suggest that ZnII activates and facilitates removal of the hydroxyl group at the Cγ position of the β-O-4 ether linkage. Activation is proposed to occur through formation of a six-membered ring complex of ZnII coordinated to the oxygen atoms at Cα and Cγ of the lignin model compound guaiacylglycerol-β-guaiacyl.