21699-53-6

Basic information

• Product Name: (+)-Neomatatabiol
• Synonyms: (+)-Neomatatabiol
• CAS NO: 21699-53-6
• Molecular Formula: C10H18O2
• Molecular Weight: 170.24872
• Mol File: 21699-53-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 251.8 °C at 760mmHg
• Flash Point: 98.9 °C
• Appearance: /
• Density: 1.009 g/cm³
• Vapor Pressure: 0.00313mmHg at 25°C
• Refractive Index: 1.475
• PKA: 13.13±0.60(Predicted)
• CAS DataBase Reference: (+)-Neomatatabiol(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Neomatatabiol(21699-53-6)
• EPA Substance Registry System: (+)-Neomatatabiol(21699-53-6)

Safety Data

• Hazardous Substances Data: 21699-53-6(Hazardous Substances Data)

Usage

General Description

(+)-Neomatatabiol is a chemical compound that belongs to the class of neolignans and is found in the roots of the tropical plant Homalomena aromatica. It has been found to have potential anti-inflammatory and anticancer properties, making it a subject of interest in medicinal research. Studies have also shown that (+)-Neomatatabiol possesses antioxidant and hepatoprotective activities, indicating its potential therapeutic value in the treatment of liver diseases. Furthermore, it has been reported to exhibit inhibitory effects on the production of nitric oxide, which has implications for its potential use in the treatment of inflammatory conditions. The compound's chemical structure and biological activities make it a promising candidate for further pharmaceutical development and investigation.

InChI:InChI=1/C10H18O2/c1-6-3-4-8-7(2)5-12-10(11)9(6)8/h6-11H,3-5H2,1-2H3/t6-,7+,8+,9+,10-/m0/s1

Upstream product

• 24512-63-8 geniposide 
• 19479-28-8 (-)-(1R)-1-methoxymyodesert-3-ene 
• 75222-58-1 (1R)-1-methoxymyodesertan 
• 26660-57-1 deoxyloganin 
• 142603-55-2 Acetic acid (1R,4aS,7S,7aR)-1-(2-ethoxy-ethoxy)-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-ylmethyl ester 
• 142603-53-0 (1R,4aS,7S,7aR)-1-(2-Ethoxy-ethoxy)-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester 
• 142603-54-1 [(1R,4aS,7S,7aR)-1-(2-Ethoxy-ethoxy)-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-yl]-methanol 
• 196509-95-2 deoxyloganin aglycone 
• 142603-56-3 (1R,4aS,7S,7aR)-1-(2-Ethoxy-ethoxy)-4,7-dimethyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran 
• 142603-57-4 (1S,4R,4aR,7S,7aR)-1-(2-Ethoxy-ethoxy)-4,7-dimethyl-octahydro-cyclopenta[c]pyran 
• 109215-55-6 (4αS,7S,7αR)nepetalactol 
• 490-09-5 (4aR,7S,7aR)-dihydronepetalactone 

Downstream Products

• 35337-15-6 (4R,4aR,7R,7aR)-4,7-Dimethyl-hexahydro-cyclopenta[c]pyran-1-one 

Relevant articles and documents

Characterization of (1R,4S,4aR,7S,7aR)-dihydronepetalactol as a semiochemical for lacewings, including Chrysopa spp. and Peyerimhoffina gracilis

The enantiomerically pure diastereoisomers (1R,4S,4aR,7S,7aR)(1) and (1R,4R,4aR,7S,7aR)-dihydronepetalactol (2) were synthesized diastereoselectively from a renewable resource, (4aS,7S,7aR)-nepetalactone (3), isolated as the main constituent of the essent

Terpenoid Chemistry. XXIV (1R)-1-Methoxymyodesert-3-ene, an Iridoid Constituent of Myoporum deserti (Myoporaceae)

A common variety of Myoporum deserti A.Cunn. (Ellangowan Poison Bush) yields an essential oil consisting largely of the iridoid monoterpene, (1R)-1-methoxymyodesert-3-ene, C11H18O2, (1R,4aS,7R,7aR)-1-methoxy-4,7-dimethyl-1,4a,5,6,7,7a-hexahydrocyclopentapyran, b.p. 67 deg/2 mm, D - 165 deg.This cyclic acetal is hydrolysed to methanol and a mixture of two epimeric cyclopentanoid dialdehydes which are oxidized to the two epimeric trans, trans-nepetalinic acids and yield (+)-(R)-actinidine with Brady's reagent, (1R)-1-Methoxymyodesert-3-ene is oxidized by ozone/hydrogen peroxide to (1R,2R,5R)-2-acetyl-5-methylcyclopentanecarboxylic acid.Hydrogenation yields mainly (1R)-methoxymyodesertan, hydrolysed by aqueous maleic acid at room temperature to methanol and a cyclic hemiacetal, (1R,4R,4aR,7R,7aR)-4,7-dimethyl-1,3,4,4a,5,6,7,7a-octahydrocyclopentapyran-1-ol.Oxidation of this cis,cis-hemiacetal by bromine in acetate buffer yields a lactone further oxidized by chromic acid to (2R,1',S',2'R,3'R)-2-(2'-carboxy-3'-methylcyclopentyl)-propionic acid. (1R)-1-Methoxymyodesertan, refluxed with aqueous phthalic acid, yields (+)-(4R,4aR,7R)-4,7-dimethyl-3,4,4a,5,6,7-hexahydrocyclopentapyran.Treatment of the hexahydropentapyran, the cis,cis-hemiacetal or (1R)-1-methoxymyodesertan with hydrochloric acid yields a trans,trans-hemiacetal, (1R,4R,4aR,7R,7aS)-4,7-dimethyl-1,3,4,4a,5,6,7,7a-octahydrocyclopentapyran-1-ol,which equilibrates in solution to a mixture of α- and β-anomers.Spectral studies of these and other products establish the configuration of the natural product at C1. (1R)-1-Methoxymyodesert-3-ene is not toxic to sheep as are the β-substituted furans characteristic of most other chemovarieties of M. deserti.