13804-51-8

Basic information

• Product Name: JH I
• Synonyms: 12,14-dihomojuvenate;2,6-tridecadienoicacid,3,11-dimethyl-10,11-epoxy-7-ethyl-,methylester,(e,e;ay22243;c18-juvenilehormone;cecropiajuvenilehormone;juvenilehormonei;methyl12,14-dihomojuvenate;methyl-12-homojuvenate
• CAS NO: 13804-51-8
• Molecular Formula: C₁₈H₃₀O₃
• Molecular Weight: 294.43
• Mol File: 13804-51-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 379.2°C at 760 mmHg
• Flash Point: 159.3°C
• Appearance: /
• Density: 0.95g/cm³
• Vapor Pressure: 5.94E-06mmHg at 25°C
• Refractive Index: nD24 1.4732
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: JH I(CAS DataBase Reference)
• NIST Chemistry Reference: JH I(13804-51-8)
• EPA Substance Registry System: JH I(13804-51-8)

Safety Data

• Hazardous Substances Data: 13804-51-8(Hazardous Substances Data)

Usage

Uses

Juvenile Hormone I is an acyclic sesquiterpenoid that regulates many aspects of insect physiology. Juvenile Hormone regulate development, reproduction, diapause, and polyphenisms.

Definition

ChEBI: A member of the juvenile hormone family of compounds that is the methyl ester of methyl (2E,6E,10R,11S)-10,11-epoxy-7-ethyl-3,11-dimethyl-2,6-tridecanoic acid.

InChI:InChI=1/C18H30O3/c1-6-15(11-12-16-18(4,7-2)21-16)10-8-9-14(3)13-17(19)20-5/h10,13,16H,6-9,11-12H2,1-5H3/b14-13+,15-10+/t16-,18+/m0/s1

Upstream product

• 52919-27-4 (2E,6E,10Z)-7-Ethyl-3,11-dimethyl-trideca-2,6,10-trienoic acid 
• 35761-89-8 (5E,9Z)-6-ethyl-10-methyl-dodeca-5,9-dien-1-yne 
• 61685-05-0 (Z)-6-methyloct-5-en-1-yne 
• 17447-02-8 (2E,6E)-methyl 3-ethyl-7-methylnona-2,6-dienoate 
• 1389395-00-9 (2Z,6E)-methyl 3,7-bis(tosyloxy)octa-2,6-dienoate 
• 1389394-98-2 (E)-methyl 3-oxo-7-(tosyloxy)oct-6-enoate 
• 1389395-08-7 C₂₄H₃₄O₆S 
• 544-97-8 dimethyl zinc(II) 
• 1389395-07-6 C₁₇H₂₈O₄ 
• 1389395-05-4 C₁₂H₂₂O₂ 
• 1389395-04-3 C₁₃H₂₂O₃ 
• 1389395-03-2 C₁₃H₂₄O₄ 
• 119678-52-3 methyl (2Z,6S,7S)-6,7-isopropylidenedioxy-7-methyl-3-phenylthio-2-nonenoate 
• 116927-03-8 (2Z,6E)-3-(Diethoxy-phosphoryloxy)-7-ethyl-9-((4S,5S)-5-ethyl-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-nona-2,6-dienoic acid methyl ester 

Downstream Products

• 33212-31-6 (-)-juvenile hormone I 
• 17793-96-3 methyl (2E,6E,10R,11S)-10,11-epoxy-7-ethyl-3,11-dimethyl-2,6-tridecanoate 
• 78-93-3 butanone 

Relevant articles and documents

Stereoselective total syntheses of insect juvenile hormones JH 0 and JH i

Total syntheses of juvenile hormones JH 0 and JH I have been achieved by a new iterative enol tosylate homologation strategy. Georg Thieme Verlag Stuttgart · New York.

SYNTHESIS OF ENANTIOMERICALLY PURE (10R, 11S)-(+)-JUVENILE HORMONES I AND II

Enantiomerically pure (+)-juvenile hormone I18JH=JH I> and (+)-juvenile hormone II 17 JH=JH II> were synthesized employing the enantioselective reduction of 2-ethyl-2-methyl-1,3-cyclohexanedione by a yeast (Pichia terricola KI0117) as the key step.

A convenient, stereospecific synthesis of racemic juvenile hormones and some of their analogues via vinylcuprates

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