(+)-Cucurbic acid

Base Information

Chemical Name:(+)-Cucurbic acid
CAS No.:58240-50-9
Molecular Formula:C₁₂H₂₀O₃
Molecular Weight:212.289
Hs Code.:
ChEMBL ID:CHEMBL2272539
DSSTox Substance ID:DTXSID401316529
Metabolomics Workbench ID:2352
Nikkaji Number:J40.306G
Wikidata:Q1143102
Mol file:58240-50-9.mol

Synonyms:(+)-cucurbic acid;58240-50-9;Cucurbic acid;(3R,6S,7S)-cucurbic acid;2-[(1R,2S,3S)-3-hydroxy-2-[(Z)-pent-2-enyl]cyclopentyl]acetic acid;CHEBI:18446;{(1R,2S,3S)-3-hydroxy-2-[(2Z)-pent-2-en-1-yl]cyclopentyl}acetic acid;131488-83-0;(+/-)-Cucurbic acid (5mg/ml in Acetonitrile);3alpha-HYDROXY-2beta-(2Z-PENTENYL)-CYCLOPENTANE-1beta-ACETIC ACID;CHEMBL2272539;DTXSID401316529;LMFA02020013;CS-0444515;C08482;T70206;Q1143102;2-((1R,2S,3S)-3-Hydroxy-2-((Z)-pent-2-en-1-yl)cyclopentyl)acetic acid

Suppliers and Price of (+)-Cucurbic acid

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

American Custom Chemicals Corporation
CUCURBIC ACID 98.00%
50MG
$ 2007.39

Total 4 raw suppliers

Chemical Property of (+)-Cucurbic acid

Chemical Property:

Vapor Pressure:8.68E-07mmHg at 25°C
Boiling Point:364.5°Cat760mmHg
Flash Point:188.4°C
PSA：57.53000
Density:1.068g/cm³
LogP:2.20450
XLogP3:1.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:212.14124450
Heavy Atom Count:15
Complexity:235

Purity/Quality:

99% ^*data from raw suppliers

CUCURBIC ACID 98.00% ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CCC=CCC1C(CCC1O)CC(=O)O
Isomeric SMILES:CC/C=C\C[C@H]1[C@H](CC[C@@H]1O)CC(=O)O
Uses (+)-Cucurbic Acid can be used as reactant/reagent for engineering and chemical process of EIMS fragmentation and MRM quantification of TMS derivatives of cucurbic acid and 6,7-stereoisomers.

Technology Process of (+)-Cucurbic acid

There total 67 articles about (+)-Cucurbic acid 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:

: 128820-28-0,807630-26-8
(1S,5S,8R)-8-<(2'Z)-pent-2'-enyl>-2-oxybicyclo<3.2.1>octan-3-on

: 34027-33-3,53369-27-0,54595-06-1,54595-07-2,54595-08-3,54595-09-4,58240-50-9,109008-59-5,117179-84-7,120330-52-1,131488-83-0,139560-28-4,143234-96-2,143234-98-4,146143-02-4
[(1S,2R,3S)-3-Hydroxy-2-((Z)-pent-2-enyl)-cyclopentyl]-acetic acid

Guidance literature:: With potassium hydroxide; water; In methanol; at 20 ℃; for 2h;
DOI:10.1080/00397919708004999

Reference yield:

: 39746-01-5
(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one

: 34027-33-3,53369-27-0,54595-06-1,54595-07-2,54595-08-3,54595-09-4,58240-50-9,109008-59-5,117179-84-7,120330-52-1,131488-83-0,139560-28-4,143234-96-2,143234-98-4,146143-02-4
[(1S,2R,3S)-3-Hydroxy-2-((Z)-pent-2-enyl)-cyclopentyl]-acetic acid

Guidance literature:: Multi-step reaction with 10 steps

1: 98 percent / benzene / 0.5 h / 20 °C

2: 71 percent / DBU / CH₂Cl₂ / 3 h / 20 °C

3: 90 percent / H₂ / Rh-Al₂O₃ / ethanol / 760 Torr

4: 98 percent / NaOH; water / methanol / 3 h / 20 °C

5: 70 percent / iodobenzene diacetate; iodine / benzene / 12.75 h / Heating; two 100W tungsten filament lamps

6: NaIO₄ / RuCl₃*H₂O / acetonitrile; CCl₄; H₂O / 12 h

7: 426 mg / benzene; methanol; hexane / 0.5 h / 20 °C

8: 410 mg / DIBAL-H / tetrahydrofuran / 3 h / -78 °C

9: 240 mg / KN(TMS)2 / tetrahydrofuran / -78 - 0 °C

10: KOH; water / methanol / 2 h / 20 °C

With potassium hydroxide; sodium hydroxide; sodium periodate; [bis(acetoxy)iodo]benzene; water; hydrogen; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; ruthenium trichloride; rhodium on alumina; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; hexane; dichloromethane; water; acetonitrile; benzene; 1: Wittig reaction / 2: Elimination / 3: Catalytic hydrogenation / 4: Hydrolysis / 5: oxidative decarboxylation / 6: Catalytic oxidation / 7: Methylation / 8: Reduction / 9: Wittig reaction / 10: Hydrolysis;
DOI:10.1080/00397919708004999

Reference yield:

: 194141-90-7
(1S,5R)-6-(2'-iodoethyl)-2-oxabicyclo[3.3.0]-oct-3-one

: 34027-33-3,53369-27-0,54595-06-1,54595-07-2,54595-08-3,54595-09-4,58240-50-9,109008-59-5,117179-84-7,120330-52-1,131488-83-0,139560-28-4,143234-96-2,143234-98-4,146143-02-4
[(1S,2R,3S)-3-Hydroxy-2-((Z)-pent-2-enyl)-cyclopentyl]-acetic acid

Guidance literature:: Multi-step reaction with 5 steps

1: NaIO₄ / RuCl₃*H₂O / acetonitrile; CCl₄; H₂O / 12 h

2: 426 mg / benzene; methanol; hexane / 0.5 h / 20 °C

3: 410 mg / DIBAL-H / tetrahydrofuran / 3 h / -78 °C

4: 240 mg / KN(TMS)2 / tetrahydrofuran / -78 - 0 °C

5: KOH; water / methanol / 2 h / 20 °C

With potassium hydroxide; sodium periodate; water; potassium hexamethylsilazane; diisobutylaluminium hydride; ruthenium trichloride; In tetrahydrofuran; methanol; tetrachloromethane; hexane; water; acetonitrile; benzene; 1: Catalytic oxidation / 2: Methylation / 3: Reduction / 4: Wittig reaction / 5: Hydrolysis;
DOI:10.1080/00397919708004999