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

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

Uses

Used in Pharmaceutical Industry:
(+)-Neomatatabiol is used as a potential therapeutic agent for various applications due to its diverse biological activities.
1. Anti-inflammatory Applications:
(+)-Neomatatabiol is used as an anti-inflammatory agent for its ability to inhibit the production of nitric oxide, which has implications for the treatment of inflammatory conditions.
2. Anticancer Applications:
(+)-Neomatatabiol is used as a potential anticancer agent due to its potential anti-inflammatory and anticancer properties, making it a subject of interest in medicinal research.
3. Antioxidant Applications:
(+)-Neomatatabiol is used as an antioxidant agent for its antioxidant activity, which may contribute to its potential therapeutic value.
4. Hepatoprotective Applications:
(+)-Neomatatabiol is used as a hepatoprotective agent for its potential therapeutic value in the treatment of liver diseases, as it has been shown to possess hepatoprotective activities.

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

• 109215-55-6 (4αS,7S,7αR)nepetalactol 
• 142603-57-4 (1S,4R,4aR,7S,7aR)-1-(2-Ethoxy-ethoxy)-4,7-dimethyl-octahydro-cyclopenta[c]pyran 
• 19479-28-8 (-)-(1R)-1-methoxymyodesert-3-ene 
• 75222-58-1 (1R)-1-methoxymyodesertan 
• 24512-63-8 geniposide 
• 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 
• 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

SYNTHESIS OF IRIDOLACTONES ISOLATED FROM SILVER VINE

The naturally occurring iridolactones, nepetalactone, isodihydronepetalactone, and iridomyrmecin are synthesized in optically active forms starting from natural glycoside geniposide.The stereogenic centers were introduced with highly stereoselective hydrogenations.

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.