81840-57-5

Basic information

• Product Name: (1E)-1-(4-hydroxy-3-methoxyphenyl)-7-phenylhept-1-en-3-one
• Synonyms: (1E)-1-(4-Hydroxy-3-methoxyphenyl)-7-phenyl-1-hepten-3-one; 1-Hepten-3-one, 1-(4-hydroxy-3-methoxyphenyl)-7-phenyl-, (1E)-
• CAS NO: 81840-57-5
• Molecular Formula: C₂₀H₂₂O₃
• Molecular Weight: 310.3869
• Mol File: 81840-57-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 495.1°C at 760 mmHg
• Flash Point: 175°C
• Density: 1.121g/cm³
• Vapor Pressure: 2E-10mmHg at 25°C
• Refractive Index: 1.592
• CAS DataBase Reference: (1E)-1-(4-hydroxy-3-methoxyphenyl)-7-phenylhept-1-en-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1E)-1-(4-hydroxy-3-methoxyphenyl)-7-phenylhept-1-en-3-one(81840-57-5)
• EPA Substance Registry System: (1E)-1-(4-hydroxy-3-methoxyphenyl)-7-phenylhept-1-en-3-one(81840-57-5)

Safety Data

• Hazardous Substances Data: 81840-57-5(Hazardous Substances Data)

Usage

Description

(1E)-1-(4-hydroxy-3-methoxyphenyl)-7-phenylhept-1-en-3-one, also known as curcumin, is a natural polyphenol compound derived from the rhizome of the Curcuma longa plant, commonly known as turmeric. It exhibits a range of biological activities, such as anti-inflammatory, antioxidant, and anti-cancer properties, making it a promising candidate for various therapeutic applications.

Uses

Used in Pharmaceutical Industry:
Curcumin is used as a therapeutic agent for the treatment of inflammatory diseases, certain types of cancer, and neurodegenerative disorders due to its anti-inflammatory, antioxidant, and anti-cancer properties.
Used in Food Industry:
Curcumin is used as a food additive and natural coloring agent, imparting a vibrant yellow color to various food products.
Used in Health and Wellness Industry:
Curcumin is used as a dietary supplement and ingredient in health and wellness products due to its potential benefits for overall health and well-being.

Upstream product

• 14171-89-2 1-phenyl-5-hexanone 
• 121-33-5 vanillin 
• 335594-16-6 1-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-7-phenyl-hept-1-en-3-one 
• 335594-14-4 1-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-7-phenyl-hept-1-en-3-ol 
• 458-36-6 trans-coniferyl aldehyde 
• 290820-47-2 (2E)-3-[4-[[tert-butyldimethylsilyl]oxy]-3-methoxyphenyl]acrylaldehyde 
• 14371-10-9 (E)-3-phenylpropenal 
• 4173-44-8 6-phenylhexa-3,5-dien-2-one 
• 3360-41-6 4-phenyl-butan-1-ol 
• 69404-94-0 O-tert-butyldimethylsilylvanillin 

Downstream Products

• 78954-23-1 1-(4'-hydroxy-3'-methoxyphenyl)-7-phenyl-3-heptanone 
• 87657-77-0 1-(4-hydroxy-3-methoxyphenyl)-7-phenyl-3-heptanol 

Relevant articles and documents

Concise and efficient total synthesis of oxyphyllacinol, yakuchione-A and yakuchione-B

A concise and efficient method for the large-scale total synthesis of oxyphyllacinol (1) has been achieved in six steps with an overall yield of 46%. Simultaneously, yakuchione-A (11) was obtained in a satisfactory yield (52%) during the process. By employing a Weinreb amide (6) as the key masonry block, yakuchione-B (13) was also constructed in a great overall yield (56%) and high purity. To overcome the challenges regarding the practical scale, high purity, and reproducibility, the synthetic route that was processed takes advantage of available materials, conventional reactions, and convenient purification methods without using column chromatography.

Synthesis of diarylheptanoids and assessment of their pungency

With the aim of correlating pungency with substituent groups on one benzene ring, various analogues of yakuchinones were synthesized by means of the Claisen-Schmidt reaction. Their pungencies were assessed by direct comparison of the threshold concentrations obtained in taste experiments. The presence of a phenolic hydroxyl group was indispensable for high pungency, while that of a 1,2-double bond of the heptanone part tended to decrease the pungency.