kaurenoic acid CAS 6730-83-2

Introduction：Basic information about kaurenoic acid CAS 6730-83-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

kaurenoic acid Basic information

• Product Name: kaurenoic acid
• Synonyms: kaurenoic acid;(-)-Kaur-16-en-18-oic acid;Cunabic acid;Kaurane-16-ene-18-oic acid;ent-Kaur-16(17)-en-19-oic acid;ent-Kaur-16-en-19-oic acid;NSC 339145;Kaur-16-en-18-oic acid,(4a)-
• CAS: 6730-83-2
• MF: C20H30O2
• MW: 302.45
• Mol File: 6730-83-2.mol

kaurenoic acid Chemical Properties

• Melting point: 171-172 °C
• Boiling point: 426.6±34.0 °C(Predicted)
• density: 1.10±0.1 g/cm3(Predicted)
• storage temp.: Sealed in dry,Store in freezer, under -20°C
• solubility: DMF: 10 mg/ml; DMSO: 25 mg/ml; DMSO:PBS (pH 7.2) (1:2): 0.3 mg/ml; Ethanol: 10 mg/ml
• form: A solid
• pka: 4.70±0.40(Predicted)
• color: White to off-white
• Major Application: metabolomics vitamins, nutraceuticals, and natural products
• InChI: 1S/C20H30O2/c1-13-11-20-10-7-15-18(2,16(20)6-5-14(13)12-20)8-4-9-19(15,3)17(21)22/h14-16H,1,4-12H2,2-3H3,(H,21,22)/t14-,15+,16+,18-,19-,20-/m1/s1
• InChIKey: NIKHGUQULKYIGE-OTCXFQBHSA-N
• SMILES: C=C1C[C@@]23CC[C@]4([H])[C@@](C(O)=O)(C)CCC[C@@]4(C)[C@]2([H])CC[C@@H]1C3

Safety Information

• WGK Germany: 3
• Storage Class: 11 - Combustible Solids

kaurenoic acid Usage And Synthesis

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.

Chemical Properties

White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from plants such as Acanthopanax Cortex (1% content) and Bletilla striata leaves.

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.

Definition

ChEBI: An ent-kaurane diterpenoid that is ent-kauran-19-oic acid in which a double bond is present at position 16(17); exhibits anticancer and anti-HIV 1 activity.

in vivo

Kaurenoic acid (1-10 mg/kg, i.g., single dose) reduces peritonitis and pain induced by lipopolysaccharides (HY-D1056) in mice^[2].
Kaurenoic acid (as a diterpene compound) is the main active ingredient in the root bark extract of A. senegalensis that exhibits anticonvulsant effects in mice^[3].

• Animal Model: Mice induced by LPS^[2]
• Dosage: 1, 3, 10 mg/kg; single dose
• Administration: i.g.
• Result: Inhibited LPS-induced mechanical and thermal hyperalgesia, suppressed MPO activity, regulated the redox state of mouse paws, inhibited the production of pro-inflammatory/pain cytokines (such as TNF-α, IL-1β, and IL-33), and enhanced the production of anti-inflammatory/analgesic cytokine IL-10.

References

[1] L.A.F. PAIVA . Anti-inflammatory effect of kaurenoic acid, a diterpene from Copaifera langsdorffii on acetic acid-induced colitis in rats[J]. Vascular pharmacology, 2002, 39 6: Pages 303-307. DOI: 10.1016/s1537-1891(03)00028-4
[2] GENEIVE E. HENRY . Kaurene diterpenes from Laetia thamnia inhibit the growth of human cancer cells in vitro[J]. Cancer letters, 2006, 244 2: Pages 190-194. DOI: 10.1016/j.canlet.2005.12.022
[3] A. C. F. SOARES. Variability of the antibacterial potential among analogue diterpenes against Gram-positive bacteria: considerations on the structure–activity relationship[J]. Canadian Journal of Chemistry, 2019, 62 1. DOI: 10.1139/cjc-2018-0369