58240-50-9

Usage

Uses

Used in Chemical Engineering:
3ALPHA-HYDROXY-2BETA-(2Z-PENTENYL)-CYCLOPENTANE-1BETA-ACETIC ACID is used as a reactant/reagent for the engineering and chemical process of EIMS fragmentation and MRM quantification of TMS derivatives of cucurbic acid and 6,7-stereoisomers. Its unique structure allows for specific interactions and reactions that can be exploited in the analysis and synthesis of various compounds.
Used in Pharmaceutical Industry:
3ALPHA-HYDROXY-2BETA-(2Z-PENTENYL)-CYCLOPENTANE-1BETA-ACETIC ACID may be used as a building block or intermediate in the synthesis of pharmaceutical compounds. Its functional groups can be modified or reacted with other molecules to create new drugs with potential therapeutic applications.
Used in Material Science:
The unique structure of 3ALPHA-HYDROXY-2BETA-(2Z-PENTENYL)-CYCLOPENTANE-1BETA-ACETIC ACID may also find applications in the development of new materials with specific properties. Its cyclopentane ring and functional groups could be used to create novel polymers, coatings, or other materials with desired characteristics for various industries.

InChI:InChI=1/C12H20O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4,9-11,13H,2,5-8H2,1H3,(H,14,15)/b4-3-/t9-,10+,11+/m1/s1

Upstream product

• 53403-88-6 (1S,5S,8R)-((Z)-8-Pent-2-enyl)-2-oxa-bicyclo[3.2.1]octan-3-one 
• 62653-84-3 methyl cucurbate methyl {(1R,2S,3S)-3-hydroxy-2-[(2Z)-pent-2-en-1-yl]cyclopentyl}acetate 
• 129971-60-4 <1R*,2S*,3R*>-1-Hydroxy-2-<(3Z)-pentenyl>-3-cyanomethylcyclopentane 
• 81355-36-4 ((3aR,4R,6R,6aR)-6-Iodo-2-oxo-hexahydro-cyclopenta[b]furan-4-yl)-acetic acid 
• 81355-35-3 cyclopent-3-ene-1,2-diacetic acid 
• 53320-29-9 (3aR*,4S*,6aS*)-(2-Oxo-hexahydrocyclopentafuran-4-yl)acetic acid 
• 69584-86-7 (2aR,5aS)-2,2a,5,5a,6,6a-Hexahydro-1aH-1-oxa-cyclopropa[f]indene 
• 81355-33-1 [(1R,2S)-2-(2-Oxo-ethyl)-cyclopent-3-enyl]-acetaldehyde 
• 3048-65-5 cis-bicyclo<4.3.0>nona-3,7-diene 
• 6228-47-3 n-propyltriphenylphosphonium bromide 
• 53921-55-4 ((3aR,4S,6aS)-2-Hydroxy-hexahydro-cyclopenta[b]furan-4-yl)-acetic acid 
• 139448-29-6 [(1R,2S,3R)-3-Methanesulfonyloxy-2-(2-trityloxy-ethyl)-cyclopentyl]-acetic acid methyl ester 
• 139448-30-9 (+)-(1R,2S,3S)-methyl 3-acetoxy-2-(2-triphenylmethoxyethyl)-1-cyclopentaneacetate 
• 139448-28-5 (+)-(1R,2S,3R)-methyl 3-hydroxy-2-(2-triphenylmethoxyethyl)-1-cyclopentaneacetate 

Downstream Products

• 1211-29-6 methyl (2-(2-pent-2Z-enyl)-3-oxocyclopentyl)acetate 
• 34027-33-3 (+/-)-Cucurbic acid 
• 2570-03-8 (+/-)-methyl trans-dihydrojasmonate 
• 2570-03-8 (+/-)-methyl dihydroepijasmonate 

Relevant academic research and scientific papers

Melanogenesis-inhibitory activity and cancer chemopreventive effect of glucosylcucurbic acid from shea (vitellaria paradoxa) kernels

Two jasmonate derivatives, glucosylcucurbic acid (1) and methyl glucosylcucurbate (2), were isolated from the MeOH extract of defatted shea (Vitellaria paradoxa; Sapotaceae) kernels. These and their deglucosylated derivatives, cucurbic acid (3) and methyl cucurbate (4), were evaluated for their melanogenesis-inhibitory and cancer chemopreventive potencies. Compounds 1, 3, and 4 exhibited potent melanogenesis-inhibitory activities in α-melanocyte-stimulating hormone (α-MSH)-stimulated B16 melanoma cells. Western-blot analysis revealed that compounds 1 and 3 reduced the protein levels of MITF (=microphthalmia-associated transcription factor), tyrosinase, TRP-1 (=tyrosine-related protein 1), and TRP-2 mostly in a concentration-dependent manner. In addition, compound 1 exhibited inhibitory effects against Epstein￡Barr virus early antigen (EBV-EA) activation induced with 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, against TPA-induced inflammation in mice, and against skin tumor promotion in an in vivo two-stage mouse skin carcinogenesis test based on 7,12-dimethylbenz[a]anthracene (DMBA) as initiator, and with TPA as promoter.

An enantiospecific synthesis of (+)-methyl epijasmonate and (-)-methyl cucurbate from L-glutamic acid

An enantiospecific route to jasmonoid natural products, (+) - methyl epijasmonate and (-) -methyl cucurbate from L-glutamic acid is reported. The key step is a 5-(3,4) ene cyclization of a functionalized 1,6-diene as chiron, which sets up three chiral centres with a high degree of diastereoselectivity.

A convenient synthesis of (-)-methyl epijasmonate

A short, enantioselective synthesis of (-)-methyl epi-jasmonate, ent-1, has been achieved starting from readily available Corey lactone aldehyde 9. The key features include the stereoselective installation of 2,3-cis- disubstituted side-chains by hydrogen

Stereoselective Synthesis of Methyl Epijasmonate

Methyl epijasmonate (1) was stereoselectively synthesized from 3-hydroxymethylcyclopentanone (7).The intramolecular alkylation of bromoketone (8) or (9) was the key step to exclusively afford thermodynamically more stable oxahydrindanone (10) or (11).Synthesis was achieved in a 6percent overall yield in 12 steps from (7).

Synthesis of Chiral Methyl Cucurbate and Its Analogs

Natural (+)-(1R,2S,3S)-methyl cucurbate (1b) and the (-)-δ-lactone of 3-epi-cucurbic acid (16) were synthesized from (+)-(1R,6S,7R)-bicyclonon-3-en-7-ol (5).Asymmetric hydrolysis of the acetate (8) of (+/-)-5 with pancreatin gave optically pure the

CUCURBIC ACID AND ITS 6,7-STEREOISOMERS

The derivatives 7-iso-cucurbic acid (7-iso-CA) and 6-epi-7-iso-cucurbic acid (6-epi-7-iso-CA) were prepared from (-)-jasmonic acid (JA) by reduction and cucurbic acid (CA) and 6-epi-cucurbic acid (6-epi--CA) from (+)-7-isojasmonic acid (7-iso-JA).The chromatographic properties (TLC, HPLC, GC) of these derivatives are described and the structures established by physical data. the extracts of different plant materials were analysed with respect to the natural occurence of JA and CA and its 6,7-stereoisomers.JA, 6-epi-CA and 6-epi-7-iso-CA were identified in female flowers of Juglans regia and JA, CA, 6-epi-CA and 6-epi-7-iso-CA in spores of Anemia phyllitidis.JA, CA, 6-epi-CA and 9,10-dihydro-JA were detected in immature caryopses of Secale cereale.In rye JA dominated in young caryopses, while CA level exceeded the amount of JA in the premature fruits.In each tissue 6-epi-CA was found to be a minor component, while CA or 6-epi-7-iso-CA represented the major components; 7-iso-Ca could not be detected.

Synthesis of 12-Oxophytodienoic Acid (12-OxoPDA) and the Compounds of its Enzymic Degradation Cascade in Plants, OPC-8:0, -6:0, -4:0 and -2:0 (epi-Jasmonic Acid), as their Methyl Esters

The synthesis of 12-Oxophytodienoic acid, and the compounds of its enzymatic degradation sequence, OPC-8:0, -6:0, -4:0 and -2:0, important plant metabolites derived from linolenic acid, is reported.The syntheses use the known cyclopent-3-ene-1,2-diacetic acid as an early intermediate, and this is derived from the Cope rearrangement of 5-vinyltrinorborn-2-ene via bicyclonona-3,7-diene.Iodolactonisation and tributyltin hydride reduction provides the key intermediate (3-oxo-2-oxabicyclooctan-6-yl)acetic acid for the OPC series, whilstphenylselenolactonisation and elimination provides the necessary unsaturated lactone (7-oxo-8-oxabicyclooct-2-en-4-yl)acetic acid for 12-oxoPDA.Members of the OPC-series were made by chain extending the saturated oxabicyclooctane acid: that for the OPC-4:0 involved double Arndt-Eistert reaction, whilst the intermediates for OPC-6:0 and -8:0 were made by Kolbe anodic crossed coupling.The lactones were than converted via their lactols, Wittig reaction, esterfication and oxidation, into the compounds of the OPC ester series, including OPC-2:0 (methyl epi-jasmonate).The unsaturate lactone 8-(7-oxo-8-oxabicyclooct-2-en-4-yl)octanoic acid required for 12-oxoPDA synthesis could also be prepared by anodic synthesis either from (7-oxo-8-oxa-bicyclooct-2-en-4-yl)acetic acid, or from its 2-phenylseleno-2,3-dihydro precursor as elimination occurred concomitantly during the reaction.Since yields were low, the unsaturated acid lactone was converted into its lactol and the (Z)-pent-2-enyl side-chain was inserted first.After TBDMS blocking of the cyclopentene hydroxy group, the side-chain was elaborated to give5-(pent-2-enyl)cyclopent-2-enylacetaldehyde and chain extension carried out by a Grignard-demesylation procedure.Sequential desilylation and depyranylation, followed by oxidation of the diol, gave 12-oxoPDA, isolated as its methyl ester.

An Efficient and Stereocontrolled Synthesis of (+/-)-Methyl Epijasmonate and (+/-)-Cucurbic Acid

The total synthesis of epijasmonoids, (+/-)-methyl epijasmonate and (+/-)-cucurbic acid, starting from norbornene was described, where a key intermediate, 5β-hydroxy-2β-methoxycarbonylmethylcyclopentane 1β-acetic acid γ-lactone was efficiently prepared via a highly regioselective Baeyer-Villiger oxidation of 7-syn-substituted norbornanone based on remote substituent control.

JASMONIC ACID-LIKE SUBSTANCES FROM THE CULTURE FILTRATE OF BOTRYODIPLODIA THEOBROMAE

Four cyclopentanoidal fatty acids were isolated from the fungus Botryodiplodia theobromae and identified as jasmonic acid-like substances.Their structures are (+)-4,5-didehydro-7-iso-jasmonic acid , ethyl (+)-7-iso-jasmonate , (1R,2S)-(+)-3-oxo-2-(2Z-pentenyl)cyclopent-1-yl-propionic acid and (1S,2S)-3-oxo-2-(2Z-pentenyl)cyclopent-1-yl-butyric acid. - Keywords: Botryodiplodia theobromae; Sphaeropsidaceae; (+)-4,5-didehydro-7-iso-jasmonic acid; ethyl (+)-7-iso-jasmonate; (1R,2S)-(+)-3-oxo-2-(2Z-pentenyl)cyclopent-1-yl-propionic acid; (1S,2S)-(+)-3-oxo-2-(2Z-pentenyl)cyclopent-1-yl-butyric acid.

(+)-7-ISO-JASMONIC ACID AND RELATED COMPOUNDS FROM BOTRYODIPLODIA THEOBROMAE

Metabolites produced by Botryodiplodia theobromae (synonym Lasiodiplodia theobromae) possessing plant growth regulating activities were shown to be 7-epimer of jasmonic acid and its derivatives. - Key Word Index: Botryodiplodia theobromae; Sphaeropsidaceae; (+)-7-iso-jasmonic acid; (+)-9,10-dihydro-7-iso-jasmonic acid; (+)-11,12-didehydro-7-iso-jasmonic acid; (+)-cucurbic acid.