Juvabione

Base Information

• Chemical Name: Juvabione
• CAS No.: 17904-27-7
• Molecular Formula: C16H26 O3
• Molecular Weight: 266.38
• Hs Code.: 2918300090
• UNII: NG8LD2D5B4
• DSSTox Substance ID: DTXSID30858798
• Nikkaji Number: J14.139I
• Wikipedia: Juvabione
• Wikidata: Q10861158
• Metabolomics Workbench ID: 69289
• Mol file: 17904-27-7.mol

Synonyms:juvabione

Chemical Property of Juvabione

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 351.9°Cat760mmHg
• Flash Point: 150.4°C
• PSA: 43.37000
• Density: 0.995g/cm³
• LogP: 3.52730
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 266.18819469
• Heavy Atom Count: 19
• Complexity: 355

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(=O)CC(C)C1CCC(=CC1)C(=O)OC
• Isomeric SMILES: C[C@H](CC(=O)CC(C)C)[C@@H]1CCC(=CC1)C(=O)OC

Technology Process of Juvabione

There total 87 articles about Juvabione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

methyl (4R,1'R,3'RS)-(+)-4-(1',5'-dimethyl-3'-hydroxyhexyl)-1-cyclohexenecarboxylate (58493-52-0,60134-56-7,60497-70-3,64314-14-3,76549-67-2,80373-62-2) → (+)-(4R)-[(S)-1,5-dimethyl-3-oxohexyl]cyclohex-1-enecarboxylic acid methyl ester (17904-27-7)

Guidance literature:

With dipyridinium dichromate; 3 A molecular sieve; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1055/s-1994-25674

Reference yield: 84.0%

(R)-4-[(R)-2-(2-Isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-cyclohex-1-enecarboxylic acid methyl ester (237736-38-8) → (+)-(4R)-[(S)-1,5-dimethyl-3-oxohexyl]cyclohex-1-enecarboxylic acid methyl ester (17904-27-7)

Guidance literature:

With trifluoroacetic acid; In chloroform;

DOI:10.1016/S0040-4039(99)00713-3

Reference yield: 78.0%

methanol (67-56-1) + (4R)-4-((1R)-1,5-dimethyl-3-oxohexyl)cyclohex-1-enecarbaldehyde (42719-55-1) → (+)-(4R)-[(S)-1,5-dimethyl-3-oxohexyl]cyclohex-1-enecarboxylic acid methyl ester (17904-27-7)

Guidance literature:

With manganese(IV) oxide; sodium cyanide; acetic acid; at 20 ℃; for 24h;

DOI:10.1039/b616641e

upstream raw materials:

methanol

(R)-4-(1,5-Dimethyl-3-oxo-hexyl)-cyclohex-1-enecarbaldehyde

4-[(R)-4-(5,5-Dimethyl-[1,3]dioxan-2-yl)-cyclohex-3-enyl]-2-isobutyl-2-methylsulfanyl-pentanoic acid

methyl (4R,1'R,3'RS)-(+)-4-(1',5'-dimethyl-3'-hydroxyhexyl)-1-cyclohexenecarboxylate

Downstream raw materials:

todomatuic acid

(+)-oxoepijuvabione

methyl (4R,1'R,3'RS)-(+)-4-(1',5'-dimethyl-3'-hydroxyhexyl)-1-cyclohexenecarboxylate

4-((R)-1,5-Dimethyl-3-oxo-hexyl)-cyclohexanecarboxylic acid methyl ester

Refernces

Plant constituents biologically active to insects. II. Javabione analogs from Abies sachalinensis Mast. (1)

10.1248/cpb.31.436

The research focused on the isolation and identification of biologically active compounds from the wood of Abies sachalinensis, a species of fir tree. The purpose of the study was to identify plant constituents that exhibit insect juvenile hormone activity, specifically focusing on (+)-juvabione and its analogs. The researchers successfully isolated (+)-juvabione and two new analogs, along with trans-4-hydroxyeinnamic acid and vanillin. The structures of the new analogs were established using chemical and spectral evidence. The chemicals used in the process included various solvents for extraction and purification, such as acetone, ether, and benzene, as well as reagents for the synthesis and analysis of the compounds, like diazomethane for methylation, chromium trioxide-pyridine complex for oxidation, and NaBH4 for reduction. The study concluded with the determination of the absolute configurations of the hydroxyl groups in the isolated compounds using Horeau's rule and by comparing the compounds to known juvenile hormone mimics. The findings contribute to the understanding of the chemical ecology of fir trees and may have implications for pest control through the use of natural juvenile hormone mimics.