573703-57-8

Basic information

• Product Name: Cyclopentaneethanol, 3-hydroxy-2-(2Z)-2-pentenyl-, (1R,2R)-rel- (9CI)
• Synonyms: Cyclopentaneethanol, 3-hydroxy-2-(2Z)-2-pentenyl-, (1R,2R)-rel- (9CI)
• CAS NO: 573703-57-8
• Molecular Formula: C12H22O2
• Molecular Weight: 198.30188
• Product Categories: CYCLOPENTANE
• Mol File: 573703-57-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclopentaneethanol, 3-hydroxy-2-(2Z)-2-pentenyl-, (1R,2R)-rel- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopentaneethanol, 3-hydroxy-2-(2Z)-2-pentenyl-, (1R,2R)-rel- (9CI)(573703-57-8)
• EPA Substance Registry System: Cyclopentaneethanol, 3-hydroxy-2-(2Z)-2-pentenyl-, (1R,2R)-rel- (9CI)(573703-57-8)

Safety Data

• Hazardous Substances Data: 573703-57-8(Hazardous Substances Data)

Upstream product

• 126664-43-5 (1R,2S,3R,2''Z)-3-(Benzyloxy)-1-(2-hydroxyethyl)-2-(2-pentenyl)cyclopentan 
• 95722-42-2 (+)-7-iso-jasmonic acid methyl ester 
• 1211-29-6 Methyl jasmonate 
• 108391-93-1 (1S,6R,9R)-9-(Benzyloxy)-3-oxabicyclo<4.3.0>nonan-2-ol 
• 126664-42-4 (1R,2R,3R)-3-(Benzyloxy)-1-(2-hydroxyethyl)-2-(2-methoxyethenyl)cyclopentan 
• 1093971-84-6 2-((1R,2S,3R)-2-((Z)-pent-2-en-1-yl)-3-((triethylsilyl)oxy)cyclopentyl)ethanol 
• 6894-38-8 jasmonic acid 
• 1211-29-6 methyl jasmonate 

Downstream Products

• 62653-85-4 (+)-7-iso-jasmonic acid succinimide ester 
• 54595-10-7 (1R,5R,8S,10Z)-(-)-8-(2-Pentenyl)-2-oxabicyclo<3.2.1>octan-3-on 

Relevant articles and documents

Stereoselective synthesis of epi-jasmonic acid, tuberonic acid, and 12-oxo-PDA

epi-Jasmonic acid (epi-JA) and tuberonic acid (TA) were synthesized from the key aldehyde, all cis-2-(2-hydroxy-5-vinylcyclopentyl)acetaldehyde (14), which was in turn prepared stereoselectively from the (1R)-acetate of 4-cyclopentene-1,3-diol (10) through SN2-type allylic substitution with CH2CHMgBr followed by Mitsunobu inversion, Eschenmoser-Claisen rearrangement, and regioselective Swern oxidation of the corresponding bis-TES ether (13). Wittig reaction of the aldehyde 14 with [Ph3P(CH 2)Me]+Br- followed by oxidation afforded epi-JA (3) stereoselectivity over the trans isomer. Similarly, TA (5) was synthesized. Furthermore, the above findings were applied successfully to improve the total efficiency of the previous synthesis of 12-oxo-PDA (1).

Easy preparation of methyl 7-epi-jasmonate and four stereoisomers of methyl cucurbate, and assessment of the stereogenic effect of jasmonate on phytohormonal activities

To test the stereogenic effect of jasmonate on phytohormonal activities, methyl 7-epi-jasmonate (1b) and four stereoisomers of methyl cucurbate were easily prepared in racemic form: epimerization at the C-7 position of a commercially available methyl jasmonate (2b) with a base and subsequent fractional distillation gave a 46:54 mixture of 1b and 2b, whose reduction gave a mixture of methyl cucurbates (3-6). This synthetic chemistry was supplemented by molecular modeling and an NMR study on 1b and 2b. An assessment of the inhibitory activities of the prepared jasmonates on growth of the second leaf sheath of rice and on seed germination of cress clarified that the cis-configuration of the C-3 and C-7 side chains of jasmonate was an important factor for the high activities. In inhibiting the seed germination of cress, methyl 6-epi-cucurbate (4) exhibited activity that was markedly higher than the other compounds tested, showing that the stereochemistry at C-6 as well as at C-3 and C-7 was strictly recognized by this bioassay.