12-Hydroxyjasmonic acid

Base Information

• Chemical Name: 12-Hydroxyjasmonic acid
• CAS No.: 140631-27-2
• Molecular Formula: C12H18O4
• Molecular Weight: 226.273
• DSSTox Substance ID: DTXSID40420561
• Nikkaji Number: J451.701F
• Wikidata: Q27117137
• Metabolomics Workbench ID: 2350
• Mol file: 140631-27-2.mol

Synonyms:12-hydroxyjasmonic acid;140631-27-2;(-)-12-hydroxyjasmonic acid;{(1R,2R)-2-[(2Z)-5-hydroxypent-2-en-1-yl]-3-oxocyclopentyl}acetic acid;(1R,2R)-12-hydroxyjasmonic acid;12-Hydroxyjasmonate;trans-12-hydroxyjasmonate;trans-12-hydroxyjasmonic acid;12OH-JA;SCHEMBL5912267;CHEBI:37420;DTXSID40420561;HY-N1033;CMC_13807;LMFA02020011;2-[(1R,2R)-2-[(Z)-5-hydroxypent-2-enyl]-3-oxocyclopentyl]acetic acid;AKOS032948598;NCGC00385243-01;CS-0016297;C21385;C21669;Q27117137;2beta-[(Z)-5-Hydroxy-2-pentenyl]-3-oxocyclopentane-1alpha-acetic acid;Cyclopentaneacetic acid, 2-[(2Z)-5-hydroxy-2-pentenyl]-3-oxo-, (1R,2R)-;Cyclopentaneacetic acid, 2-(5-hydroxy-2-pentenyl)-3-oxo-, [1R-[1alpha,2beta(Z)]]-

Chemical Property of 12-Hydroxyjasmonic acid

Chemical Property:

• Vapor Pressure: 3.52E-09mmHg at 25°C
• Refractive Index: 1.514
• Boiling Point: 429.5 °C at 760 mmHg
• PKA: 4.52±0.10(Predicted)
• Flash Point: 227.7 °C
• PSA: 74.60000
• Density: 1.156 g/cm³
• LogP: 1.38510
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 226.12050905
• Heavy Atom Count: 16
• Complexity: 283

Purity/Quality:

98%min ^*data from raw suppliers

12-Hydroxyjasmonicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)C(C1CC(=O)O)CC=CCCO
• Isomeric SMILES: C1CC(=O)[C@@H]([C@H]1CC(=O)O)C/C=C\CCO

Technology Process of 12-Hydroxyjasmonic acid

There total 49 articles about 12-Hydroxyjasmonic 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: 100.0%

methyl (1S,2R,2'Z)-2-(5-hydroxy-2-pentenyl)-3-oxo-cyclopentaneacetate (179915-48-1) → [(1R,2R,2'Z)-2-(5'-hydroxypent-2'-enyl)-3-oxocyclopentane]acetic acid (140631-27-2)

Guidance literature:

methyl (1S,2R,2'Z)-2-(5-hydroxy-2-pentenyl)-3-oxo-cyclopentaneacetate; With potassium hydroxide; water; In methanol; at 90 ℃;

With hydrogenchloride; In methanol; water;

DOI:10.1271/bbb.80338

Reference yield: 79.0%

12-hydroxy-epi-jasmonic acid (124649-26-9) → [(1R,2R,2'Z)-2-(5'-hydroxypent-2'-enyl)-3-oxocyclopentane]acetic acid (140631-27-2)

Guidance literature:

With sodium hydroxide; In methanol; water; at 20 ℃; for 2h;

DOI:10.1039/c0ob00218f

Reference yield:

{(1R,2R,2'Z)-2-[5'-(β-D-glucopyranosyloxy)pent-2'-enyl]-3-oxocyclopentane}acetic acid (120399-24-8) → β-D-glucose (492-61-5) + [(1R,2R,2'Z)-2-(5'-hydroxypent-2'-enyl)-3-oxocyclopentane]acetic acid (140631-27-2)

Guidance literature:

With TAG β-glucosidase; In water; Enzymatic reaction;

DOI:10.1016/j.abb.2015.07.021

upstream raw materials:

(-)N-(12-Acetoxy)jasmonoyl-phenylalaninmethylester

2-((1R,2S)-3-oxo-2-((Z)-5-(tetrahydro-2H-pyran-2-yloxy)-pent-2-enyl)cyclopentyl)ethanoic acid

12-hydroxy-epi-jasmonic acid

(1R,2S,3R)-1-triethylsilyloxy-2-(2-triethylsilyloxyethyl)-3-vinylcyclopentane

Downstream raw materials:

(Z)-1,2-trans-8,13-dioxo-7-oxabicyclo<8.3.0>tridec-3-ene

Refernces

• 1、 Nonaka, Hisato,Ogawa, Narihito,Maeda, Noriaki,Wang, Yong-Gang,Kobayashi, Yuichi. "Stereoselective synthesis of epi-jasmonic acid, tuberonic acid, and 12-oxo-PDA". experimental part. p. 5212 - 5223. Retrieved 2010/12/25.
• 2、 Nakamura, Yoko,Miyatake, Ryoji,Inomata, Sho,Ueda, Minoru. "Synthesis and bioactivity of potassium β-D-glucopyranosyl 12-hydroxy jasmonate and related compounds". experimental part. p. 2867 - 2876. Retrieved 2009/04/11.