17092-92-1

Basic information

• Product Name: (2,6,6-Trimethyl-2-hydroxycyclohexylidene)acetic acid lactone
• Synonyms: (2,6,6-TriMethyl-2-hydroxycyclohexylidene)acetic acid laCLone;(2,6,6-Trimethyl-2-hydroxycyclohexylidene)acetic acid lacton;2(4H)-Benzofuranone;2(4H)-Benzofuranone, 5,6,7,7a-tetrahydro-4,4,7a-trimethyl-;2(4H)-Benzofuranone, 5,6,7,7a-tetrahydro-4,4,7a-trimethyl-, (R)-;2(4H)-Benzofuranone, 5,6,7,7a-tetrahydro-4,4,7a-trimethyl-, (S)-;Actinidiolide, dihydro-;dihydroactindiolide
• CAS NO: 17092-92-1
• Molecular Formula: C₁₁H₁₆O₂
• Molecular Weight: 180.24
• EINECS: 239-390-4
• Product Categories: ester Flavor
• Mol File: 17092-92-1.mol
• Article Data: 24

Chemical Properties

• Melting Point: 70-71°
• Boiling Point: 296.099 °C at 760 mmHg
• Flash Point: 120.249 °C
• Appearance: Colorless crystal
• Density: 1.058 g/cm³
• Vapor Pressure: 0.00147mmHg at 25°C
• Refractive Index: 1.504
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: (2,6,6-Trimethyl-2-hydroxycyclohexylidene)acetic acid lactone(CAS DataBase Reference)
• NIST Chemistry Reference: (2,6,6-Trimethyl-2-hydroxycyclohexylidene)acetic acid lactone(17092-92-1)
• EPA Substance Registry System: (2,6,6-Trimethyl-2-hydroxycyclohexylidene)acetic acid lactone(17092-92-1)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 17092-92-1(Hazardous Substances Data)

Usage

Biological activity

Dihydroactinidiolide is present in plant leaves and fruits, is a potent plant growth inhibitor, a regulator of gene expression, and is also responsible for light adaptation in Arabidopsis. Dihydroactinidiolide has antioxidant activity, antibacterial activity, anticancer activity and neuroprotection.

Use

Dihydroactinidiolide is an ester organic matter, which can be used as a food flavor.

InChI:InChI=1/C11H16O2/c1-10(2)5-4-6-11(3)8(10)7-9(12)13-11/h7H,4-6H2,1-3H3

Upstream product

• 16778-27-1 4,4,7a-trimethylhexahydro-1-benzofuran-2(3H)-one 
• 29951-40-4 (+/-)-aeginetolide 
• 472-66-2 (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde 
• 472-68-4 (2,6,6-trimethylcyclohex-1-enyl)acetic acid 
• 7235-40-7 beta-carotene 
• 302-79-4 all-trans-retinoic-acid 
• 58937-20-5 1-acetoxy-2-(2,6,6-trimethyl-1-cyclohexen-1-yl)-ethene 
• 130921-05-0 (Dimethoxy-phosphoryl)-acetic acid 1,3,3-trimethyl-2-oxo-cyclohexyl ester 
• 120211-66-7 2,2-Diethoxy-4,4,7a-trimethyl-4,5,6,7,7a-pentahydro-2H-benzofuran 
• 19432-07-6 (+/-) aeginetolide 
• 20013-73-4 2,6,6-trimethylcyclohex-2-en-1-one 
• 113832-63-6 (+/-)-(1-hydroxy-2,6,6-trimethyl-2-cyclohexenyl)acetic acid 
• 113832-62-5 2-(1-Hydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)ethansaeure-ethylester 
• 1193-18-6 3-methylcyclohexen-2-one 

Downstream Products

• 1258783-37-7 C₁₁H₂₀O₂ 

Relevant articles and documents

Dihydroactinidiolide, a natural product against Aβ25-35 induced toxicity in Neuro2a cells: Synthesis, in silico and in vitro studies

Synthesis of natural products has speeded up drug discovery process by minimizing the time for their purification from natural source. Several diseases like Alzheimer's disease (AD) demand exploring multi targeted drug candidates, and for the first time we report the multi AD target inhibitory potential of synthesized dihydroactinidiolide (DA). Though the activity of DA in several solvent extracts have been proved to possess free radical scavenging, anti bacterial and anti cancer activities, its neuroprotective efficacy has not been evidenced yet. Hence DA was successfully synthesized from β-ionone using facile two-step oxidation method. It showed potent acetylcholinesterase (AChE) inhibition with half maximal inhibitory concentration (IC50) 34.03 nM, which was further supported by molecular docking results showing strong H bonding with some of the active site residues such as GLY117, GLY119 and SER200 of AChE. Further it displayed DPPH and (.NO) scavenging activity with IC50 value 50 nM and metal chelating activity with IC50 >270 nM. Besides, it significantly prevented amyloid β25-35 self-aggregation and promoted its disaggregation at 270 nM. It did not show cytotoxic effect towards Neuro2a (N2a) cells up to 24 h at 50 and 270 nM while it significantly increased viability of amyloid β25-35 treated N2a cells through ROS generation at both the concentrations. Cytotoxicity profile of DA against human PBMC was quite impressive. Hemolysis studies also revealed very low hemolysis i.e. minimum 2.35 to maximum 5.61%. It also had suitable ADME properties which proved its druglikeness. The current findings demand for further in vitro and in vivo studies to develop DA as a multi target lead against AD.

Cu(I)-catalyzed oxidative cyclization of alkynyl oxiranes and oxetanes

In the presence of a Cu(I) catalyst and a pyridine oxide, alkynyl oxiranes and oxetanes can be converted into functionalized five- or six-membered α,β-unsaturated lactones or dihydrofuranaldehydes. This new oxidative cyclization is proposed to proceed via an unusual allenyloxypyridinium intermediate.

Total synthesis of (±)-dihydroactinidiolide using selenium-stabilized carbenium ion

A new, short total synthesis of dihydroactinidiolide 1 is described using selenium carbenium ion-promoted carbon-carbon bond formation as the key step. Our synthetic strategy starts with a lactonization reaction between 1,3,3-trimethylcyclohexene 13 and α-chloro-α-phenylseleno ethyl acetate 14, affording the key intermediate, α-phenylseleno-γ-butyro lactone 15, which reacted via a selenoxide elimination to the target compound 1.