36062-05-2

Basic information

• Product Name: HEXAHYDROCURCUMIN
• Synonyms: HEXAHYDROCURCUMIN;1,7-Bis(3-methoxy-4-hydroxyphenyl)-5-hydroxy-3-heptanone;1,7-Bis(4-hydroxy-3-methoxyphenyl)-5-hydroxyheptan-3-one;5-Hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3-heptanone;5-Hydroxy-1-(4-hydroxy-3-Methoxycyclohexyl)-7-(4-hydroxy-3-Methoxyphenyl)heptan-3-one;(RS)-5-Hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3-heptanone
• CAS NO: 36062-05-2
• Molecular Formula: C₂₁H₂₆O₆
• Molecular Weight: 374.42754
• Mol File: 36062-05-2.mol
• Article Data: 23

Chemical Properties

• Melting Point: 80-82℃
• Boiling Point: 622.6°C at 760 mmHg
• Flash Point: 218℃
• Appearance: /
• Density: 1.226
• Vapor Pressure: 2.31E-16mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly), DCM, DMSO
• PKA: 10.02±0.20(Predicted)
• BRN: 2486876
• CAS DataBase Reference: HEXAHYDROCURCUMIN(CAS DataBase Reference)
• NIST Chemistry Reference: HEXAHYDROCURCUMIN(36062-05-2)
• EPA Substance Registry System: HEXAHYDROCURCUMIN(36062-05-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 36062-05-2(Hazardous Substances Data)

Usage

Description

Hexahydrocurcumin is a natural product and glucuronide metabolite of curcumin that has anti-inflammatory, antioxidant, and anticancer properties. It reduces prostaglandin E2 (PGE2) production stimulated by phorbol 12-myristate 13-acetate (PMA; ) by 37% in human colonic epithelial cells when used at a concentration of 20 μM. Hexahydrocurcumin (3.125-25 μM) inhibits overproduction of nitric oxide induced by LPS in RAW 264.7 macrophage cells in a concentration-dependent manner. It does not affect LPS-induced cytokine release but inhibits LPS-induced iNOS and COX-2 upregulation and NF-κB activation when used at a concentration of 50 μM. Hexahydrocurcumin prevents the formation of aberrant crypt foci in a dimethylhydrazine rat model of colon cancer and potentiates the effect of 5-fluorouracil .

Uses

Hexahydrocurcumin is an intermediate in the synthesis of Gingerenone A (G387500) which is an antifungal and antiparasitic diarylheptenone that is isolated from Zingiber officinale (more commonly known as ginger), a medicinal plant that is used to treat inflammation and musculoskeletal disorders.

InChI:InChI=1/C21H26O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h5-6,9-12,16,22,24-25H,3-4,7-8,13H2,1-2H3

Upstream product

• 98885-93-9 curcumin 
• 458-37-7 curcumin 
• 93559-23-0 4-(2-{2-[4-(4-Benzyloxy-3-methoxy-phenyl)-2-hydroxy-butyl]-[1,3]dioxolan-2-yl}-ethyl)-2-methoxy-phenol 
• 36062-04-1 1,7-bis(4-hydroxy-3-methoxyphenyl)-heptane-3,5-dione 
• 869101-60-0 O,O-di-t-butyloxycarbonylhexahydrocurcumin 
• 70727-06-9 (Z)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hept-4-en-3-one 
• 147556-16-9 curcumin 
• 121-33-5 vanillin 
• 123-54-6 acetylacetone 
• 91827-17-7 {2-[2-(4-Hydroxy-3-methoxy-phenyl)-ethyl]-[1,3]dioxolan-2-yl}-acetaldehyde 
• 115945-70-5 glucose 
• 1360110-05-9 (S)-1,7-bis(4-hydroxy-3-methoxyphenyl)-5-(methoxymethoxy)heptan-3-one 
• 1360109-97-2 (S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(4-(benzyloxy)-3-methoxyphenyl)-3-hydroxypentan-1-one 
• 1360109-98-3 (S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(4-(benzyloxy)-3-methoxyphenyl)-3-(methoxymethoxy)pentan-1-one 

Downstream Products

• 79067-88-2 (E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-hepten-3-one 
• 41137-87-5 hirsutenone 
• 135308-89-3 Acetic acid 4-[(3S,5R)-3,5-diacetoxy-7-(4-acetoxy-3-methoxy-phenyl)-heptyl]-2-methoxy-phenyl ester 
• 79067-88-2 1,7-bis-(4-hydroxy-3-methoxyphenyl)-4-hepten-3-one 
• 153381-09-0 (3R,5S)-3,5-Dihydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane 
• 112494-41-4 (3S,5S)-3,5-Dihydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane 

Relevant articles and documents

Hexahydrocurcumin ameliorates hypertensive and vascular remodeling in L-NAME-induced rats

Hexahydrocurcumin (HHC), a major metabolite of curcumin, possesses several biological activities such as antioxidant, anti-inflammation, and cardioprotective properties. This study aimed to investigate the effect of HHC on high blood pressure, vascular dy

Use of curcumin derivative

The invention provides the use of a curcumin derivative. The use of the curcumin derivative shown in a formula I (please see the specification for the formula), or salts of the curcumin derivative inthe preparation of drugs of anti-inflammatory diseases and/or a COX inhibitor is particularly provided. The curcumin derivative has good COX inhibitory activity and anti-inflammatory activity and canbe used for preparing the COX inhibitor and anti-inflammatory drugs. Compound 6 and compound 7 have the best effects on COX-2 inhibitory activity and anti-inflammatory activity and can be used for preparing a COX-2 inhibitor and the anti-inflammatory drugs.

Synthesis and evaluation of curcumin derivatives toward an inhibitor of beta-site amyloid precursor protein cleaving enzyme 1

To research a new non-peptidyl inhibitor of beta-site amyloid precursor protein cleaving enzyme 1, we focused on the curcumin framework, two phenolic groups combined with an sp2 carbon spacer for low-molecular and high lipophilicity. The structure-activity relationship study of curcumin derivatives is described. Our results indicate that phenolic hydroxy groups and an alkenyl spacer are important structural factors for the inhibition of beta-site amyloid precursor protein cleaving enzyme 1 and, furthermore, non-competitive inhibition of enzyme activity is anticipated from an inhibitory kinetics experiment and docking simulation.