ent-Kaur-16-en-19-oic acid

Base Information

• Chemical Name: ent-Kaur-16-en-19-oic acid
• CAS No.: 6730-83-2
• Molecular Formula: C₂₀H₃₀O₂
• Molecular Weight: 302.457
• UNII: D572D9R2TZ
• DSSTox Substance ID: DTXSID801024912
• Wikipedia: Kaurenoic_acid
• Metabolomics Workbench ID: 28546
• ChEMBL ID: CHEMBL523791
• Mol file: 6730-83-2.mol

Synonyms:3beta-hydroxy-kaurenoic acid;ent-kaur-16-en-18-oic acid;kaur-16-en-18-oic acid;kaurenoic acid

Chemical Property of ent-Kaur-16-en-19-oic acid

Chemical Property:

• Vapor Pressure: 1.79E-08mmHg at 25°C
• Melting Point: 171-172 °C
• Boiling Point: 426.6°C at 760 mmHg
• PKA: 4.70±0.40(Predicted)
• Flash Point: 202.8°C
• PSA: 37.30000
• Density: 1.1g/cm³
• LogP: 5.04010
• Storage Temp.: ?20°C
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 302.224580195
• Heavy Atom Count: 22
• Complexity: 538

Purity/Quality:

99.5% ^*data from raw suppliers

ent-KaurenoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCCC(C1CCC34C2CCC(C3)C(=C)C4)(C)C(=O)O
• Isomeric SMILES: C[C@@]12CCC[C@@]([C@H]1CC[C@]34[C@H]2CC[C@@H](C3)C(=C)C4)(C)C(=O)O
• Description: Kaurenoic acid is a diterpene that has been found in C. langsdorffii and has diverse biological activities, including anticancer, antibacterial, antioxidant, and anti-inflammatory properties. It is cytotoxic to 22Rv1 and LNCaP prostate, HT-29, HCT116, SW480, and SW620 colon, and MCF-7 breast cancer cells with IC50 values ranging from 15.03 to 48.87 μg/ml. Kaurenoic acid is active against S. epidermidis, S. capitis, E. faecalis, and S. haemolyticus in vitro (MICs = 6.25-12.5 μg/ml). Kaurenoic acid (50 and 100 mg/kg) reduces colonic myeloperoxidase (MPO) activity and malondialdehyde (MDA) levels in a rat model of acetic acid-induced colitis, as well as colonic tissue damage, leukocytic infiltration, and submucosal edema when administered at a dose of 100 mg/kg.
• Uses: ent-Kaurenoic Acid can be used in biological study. Kinetic profile of guaco syrup metabolites like coumarin, 7-hydroxycoumarin, o-coumaric acid, kaurenoic acid can be performed for identification of alternative route of coumarin metabolism in human plasma.

Technology Process of ent-Kaur-16-en-19-oic acid

There total 32 articles about ent-Kaur-16-en-19-oic 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:

D,L-mevalonic acid (150-97-0,690-72-2,17817-88-8,32451-23-3) → kaurene (469-85-2,469-86-3,562-28-7,10178-84-4,13850-19-6,20070-61-5,87759-99-7) + gibberellin A12 (1164-45-0) + kaurenoic acid (5095-09-0,6730-83-2,14046-76-5,19941-50-5,20316-84-1,34426-48-7,98523-71-8) + ent-kaura-6,16-dien-19-oic acid (77280-78-5)

Guidance literature:

With cell-free system of Phaseolus coccineus; K-Pi buffer; NADPH; bovine serum albumin; at 28 - 30 ℃; for 2h; Further byproducts given;

Reference yield:

C20H31IO2 (55102-94-8) → kaurenoic acid (5095-09-0,6730-83-2,14046-76-5,19941-50-5,20316-84-1,34426-48-7,98523-71-8)

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide;

DOI:10.1016/S0040-4020(01)97052-8

Reference yield:

C27H38O5S → kaurenoic acid (5095-09-0,6730-83-2,14046-76-5,19941-50-5,20316-84-1,34426-48-7,98523-71-8)

Guidance literature:

Multi-step reaction with 2 steps

1: NaI / acetone

2: KOtBu / dimethylsulfoxide

With potassium tert-butylate; sodium iodide; In dimethyl sulfoxide; acetone;

DOI:10.1016/S0040-4020(01)97052-8

upstream raw materials:

3-hydroxy-3-methylpentanoic acid

D,L-mevalonic acid

kaurene

(-)-kaur-16-en-19-ol

Downstream raw materials:

17α,19-Dihydroxy-ent-kauran

C₂₁H₃₄O₃

methyl ent-15β-hydroxy-16α-kauran-19-oate

methyl ent-15-oxokauran-19-oate

Refernces

• 1、 Hedden, Peter,Graebe, Jan E.. "KAURENOLIDE BIOSYNTHESIS IN A CELL-FREE SYSTEM FROM CUCURBITA MAXIMA SEEDS". . p. 1011 - 1016. Retrieved 2007/10/02.