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

Description

3-(4-Hydroxy-3-methoxy-phenyl)-propionaldehyde, commonly known as Hydroxyisohexyl 3-cyclohexene carboxaldehyde or Lyral, is a synthetic fragrance ingredient characterized by its floral, green, and creamy odor profile. It is widely used in cosmetics and personal care products, including perfumes, soaps, and lotions. However, its use has been restricted or banned in certain regions due to potential health risks, such as skin sensitization, allergic reactions, and respiratory sensitization.

Uses

Used in Cosmetics and Personal Care Products:
3-(4-Hydroxy-3-methoxy-phenyl)-propionaldehyde is used as a fragrance ingredient in cosmetics and personal care products for its distinctive floral, green, and creamy scent. It enhances the sensory experience of these products, making them more appealing to consumers.
Used in Perfumes:
In the perfume industry, 3-(4-Hydroxy-3-methoxy-phenyl)-propionaldehyde is used as a key component in creating complex and long-lasting fragrances. Its unique scent profile contributes to the overall aroma of perfumes, providing a pleasant and memorable olfactory experience.
Used in Soaps and Lotions:
3-(4-Hydroxy-3-methoxy-phenyl)-propionaldehyde is used as a fragrance ingredient in soaps and lotions, imparting a pleasant and refreshing scent to these products. Its incorporation enhances the overall sensory experience, making these products more enjoyable to use.
However, due to the potential health risks associated with 3-(4-Hydroxy-3-methoxy-phenyl)-propionaldehyde, such as skin sensitization and allergic reactions, some companies have opted to phase out its use in favor of safer alternatives. This decision aims to protect consumer health and ensure the safety of cosmetic and personal care products.

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 
• 4046-02-0 ethyl 4-hydroxy-3-methoxycinnamate 
• 56024-44-3 methyl 3-(4-hydroxy-3-methoxyphenyl)propanoate 
• 1135-23-5 3-(4-hydroxy-3-methoxyphenyl)propionic acid 

Downstream Products

• 112798-58-0 γ-(4-Oxy-3-methoxy-phenyl)-propylamin 

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.