61521-74-2

Basic information

• Product Name: (3R)-3β,4α-Bis(3-methoxy-4-hydroxybenzyl)-3-hydroxytetrahydrofuran-2-one
• Synonyms: (3R)-3β,4α-Bis(3-methoxy-4-hydroxybenzyl)-3-hydroxytetrahydrofuran-2-one;(3R,4R)-3,4-Bis(4-hydroxy-3-methoxybenzyl)-3-hydroxy-4,5-dihydrofuran-2(3H)-one;(3R,4R)-4,5-Dihydro-3,4-bis(3-methoxy-4-hydroxybenzyl)-3-hydroxyfuran-2(3H)-one;(3R,4R)-4,5-Dihydro-3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]furan-2(3H)-one
• CAS NO: 61521-74-2
• Molecular Formula: C₂₀H₂₂O₇
• Molecular Weight: 374.38
• Mol File: 61521-74-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 633.437 °C at 760 mmHg
• Flash Point: 226.73 °C
• Appearance: /
• Density: 1.37 g/cm³
• Vapor Pressure: 6.47E-17mmHg at 25°C
• Refractive Index: 1.629
• CAS DataBase Reference: (3R)-3β,4α-Bis(3-methoxy-4-hydroxybenzyl)-3-hydroxytetrahydrofuran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3R)-3β,4α-Bis(3-methoxy-4-hydroxybenzyl)-3-hydroxytetrahydrofuran-2-one(61521-74-2)
• EPA Substance Registry System: (3R)-3β,4α-Bis(3-methoxy-4-hydroxybenzyl)-3-hydroxytetrahydrofuran-2-one(61521-74-2)

Safety Data

• Hazardous Substances Data: 61521-74-2(Hazardous Substances Data)

Usage

Description

(3R)-3β,4α-Bis(3-methoxy-4-hydroxybenzyl)-3-hydroxytetrahydrofuran-2-one, also known as tetrahydrocurcumin, is a naturally occurring compound found in the rhizomes of the turmeric plant (Curcuma longa). It is a derivative of curcumin, the active ingredient in turmeric, and is known for its antioxidant, anti-inflammatory, and anti-cancer properties.
Used in Pharmaceutical Industry:
Tetrahydrocurcumin is used as a therapeutic agent for its potential health benefits, including its ability to reduce oxidative stress, inhibit inflammation, and provide protection against various chronic diseases.
Used in Skincare Industry:
Tetrahydrocurcumin is used as a treatment for various skin disorders due to its anti-inflammatory and antioxidant properties.
Used in Diabetes Treatment:
Tetrahydrocurcumin is used as a therapeutic agent for diabetes, as it has been studied for its potential to improve insulin sensitivity and glucose metabolism.
Used in Neurodegenerative Disease Treatment:
Tetrahydrocurcumin is used as a potential therapeutic agent for neurodegenerative diseases, as it has been investigated for its potential to protect against neuronal damage and improve cognitive function.
Used in Cancer Treatment:
Tetrahydrocurcumin is used as a potential therapeutic agent in the treatment of various types of cancer, as it has been studied for its ability to inhibit cancer cell growth and induce apoptosis.

InChI:InChI=1/C20H22O7/c1-25-17-8-12(3-5-15(17)21)7-14-19(23)27-11-20(14,24)10-13-4-6-16(22)18(9-13)26-2/h3-6,8-9,14,21-22,24H,7,10-11H2,1-2H3/t14-,20-/m0/s1

Upstream product

• 116185-13-8 (3S,4S)-3,4-Bis-(4-benzyloxy-3-methoxy-benzyl)-dihydro-furan-2,5-dione 
• 111194-07-1 trans-(+/-)-dihydro-3,4-bis<<3-methoxy-4-(phenylmethoxy)phenyl>methyl>-2(3H)-furanone 
• 116185-11-6 benzyl 3-[4-(benzyloxy)-3-methoxyphenyl]propanoate 
• 116185-12-7 2,3-bis<<3-methoxy-4-(phenylmethoxy)phenyl>methyl>-butanedioic acid 
• 30034-49-2 β-(4-benzyloxy-3-methoxyphenyl)propionic acid 
• 1135-23-5 3-(4-hydroxy-3-methoxyphenyl)propionic acid 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 116185-15-0 dihydro-3-hydroxy-3,4-bis<<3-methoxy-4-(phenylmethoxy)phenyl>methyl>-2,(3H)-furanone 
• 336101-59-8 (2R,2'S,4'S)-2-{4-[4-(benzyloxy)-3-methoxybenzyl]-2-(tert-butyl)-5-oxo-1,3-dioxolan-4-yl}-3-[4'-(benzyloxy)-3'-methoxyphenyl]propanoic acid 
• 336101-58-7 (R)-3-(4-Benzyloxy-3-methoxy-phenyl)-2-((2S,4S)-2-tert-butyl-5-oxo-[1,3]dioxolan-4-yl)-propionic acid 
• 336101-52-1 (2R,3S)-2-[4-(benzyloxy)-3-methoxybenzyl]-3-hydroxybutanedioic acid diisopropyl ester 
• 336101-54-3 (2R,3S)-2-(4-Benzyloxy-3-methoxy-benzyl)-3-hydroxy-succinic acid 
• 111194-07-1 (3R,4R)-3,4-bis(4-benzyloxy-3-methoxybenzyl)dihydrofuran-2(3H)-one 
• 111266-03-6 (R)-(+)-3-(4-benzyloxy-3-methoxybenzyl)-γ-butyrolactone 

Downstream Products

• 33464-73-2 3,4-bis<(3,4-dimethoxyphenyl)methyl>dihydro-3-hydroxy-2(3H)-furanone 
• 33464-73-2 3,4-bis<(3,4-dimethoxyphenyl)methyl>dihydro-3-hydroxy-2(3H)-furanone 
• 58139-12-1 7-hydroxysecoisolariciresinol 
• 33464-73-2 (-)-O-methyltrachelogenine 
• 146196-54-5 (-)-O-dimethyltrachelogenine 

Relevant articles and documents

Radical and superoxide scavenging activities of matairesinol and oxidized matairesinol

The radical and superoxide scavenging activities of oxidized matairesinols were examined. It could be assumed that the free benzylic position was important for higher radical scavenging activity. The different level of activity was observed between 7′-oxomatairesinol (Mat 2) and 7-oxomatairesinol (Mat 3). The activity of 8-hydroxymatairesinol was lower than that of matairesinol (Mat 1). The superoxide scavenging activity of the oxidized matairesinols was also demonstrated for the first time. It is assumed that the pKa value of phenol in the oxidized matairesinols affected this activity.

Synthesis of (+)-wikstromol by double alkylation of malic acid

The synthesis of (+)-wikstromol in six steps, based on two stereoselective benzylations of unnatural malic acid derivatives, is presented. The influence of the alkyl ester on yield and selectivity in the alkylation of malic acid esters is examined.

TOTAL SYNTHESES OF (-)-TRACHELOGENIN, (-)-NORTRACHELOGENIN AND (+)-WIKSTROMOL

The title compounds were obtained by α-hydroxylation of the corresponding α,β-dibenzyl-γ-butyrolactones (lignans of synthetic origin), and were correlated to (+/-)-methyltrachelogenin 9 whose relative structure was definitely established by X-ray cristallography. (-)-Trachelogenin 1 and (-)-nortrachelogenin 12 thus have the (8S,8'S) absolute configuration, whereas (+)-nortrachelogenin 20 (or wikstromol) has the (8R,8'R) absolute configuration.