Kaurenoic acid
featured

    WARNING: This product is for research use only, not for human or veterinary use.

Hodoodo CAT#: H558137

CAS#: 6730-83-2

Description: Kaurenoic acid is a bioactive chemical.

Chemical Structure

img
Kaurenoic acid
CAS# 6730-83-2
Instruction

Theoretical Analysis

Hodoodo Cat#: H558137
Name: Kaurenoic acid
CAS#: 6730-83-2
Chemical Formula: C20H30O2
Exact Mass: 302.22
Molecular Weight: 302.460
Elemental Analysis: C, 79.42; H, 10.00; O, 10.58

Price and Availability

Size Price Availability Quantity
10mg USD 320 2 Weeks
20mg USD 550 2 Weeks
Bulk inquiry

Synonym: CCRIS 1514; Kauren-19-oic acid;

IUPAC/Chemical Name: (4R,4aS,6aS,9S,11aR,11bS)-4,11b-dimethyl-8-methylenetetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid

InChi Key: NIKHGUQULKYIGE-SHAPNJEPSA-N

InChi Code: 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+/m0/s1

SMILES Code: C1(C[C@@]23[C@H]([C@@]4(CCC[C@]([C@H]4CC3)(C(=O)O)C)C)CC[C@H]1C2)=C

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 302.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Miyazaki S, Nakajima M, Kawaide H. Hormonal diterpenoids derived from ent-kaurenoic acid are involved in the blue-light avoidance response of Physcomitrella patens. Plant Signal Behav. 2015;10(2):e989046. doi: 10.4161/15592324.2014.989046. PubMed PMID: 25751581; PubMed Central PMCID: PMC4622475.

2: Silva JJ, Pompeu DG, Ximenes NC, Duarte AS, Gramosa NV, Carvalho Kde M, Brito GA, Guimarães SB. Effects of Kaurenoic Acid and Arginine on Random Skin Flap Oxidative Stress, Inflammation, and Cytokines in Rats. Aesthetic Plast Surg. 2015 Dec;39(6):971-7. doi: 10.1007/s00266-015-0559-8. Epub 2015 Sep 25. PubMed PMID: 26408387.

3: Miranda MM, Panis C, da Silva SS, Macri JA, Kawakami NY, Hayashida TH, Madeira TB, Acquaro VR Jr, Nixdorf SL, Pizzatti L, Ambrósio SR, Cecchini R, Arakawa NS, Verri WA Jr, Costa IC, Pavanelli WR. Kaurenoic Acid Possesses Leishmanicidal Activity by Triggering a NLRP12/IL-1β/cNOS/NO Pathway. Mediators Inflamm. 2015;2015:392918. doi: 10.1155/2015/392918. Epub 2015 May 13. PubMed PMID: 26074677; PubMed Central PMCID: PMC4444587.

4: Miyazaki S, Kimura H, Natsume M, Asami T, Hayashi KI, Kawaide H, Nakajima M. Analysis of ent-kaurenoic acid by ultra-performance liquid chromatography-tandem mass spectrometry. Biochem Biophys Rep. 2015 May 30;2:103-107. doi: 10.1016/j.bbrep.2015.05.010. eCollection 2015 Jul. PubMed PMID: 29124150; PubMed Central PMCID: PMC5668645.

5: Agostini-Costa TD, Gomes IS, Fonseca MC, Alonso AM, Pereira RC, Montanari Junior I, da Silva JP, Pereira AM, da Silva DB, Vieira RF, Vaz AP. Effect of Accessions and Environment Conditions on Coumarin, O-Coumaric and Kaurenoic Acids Levels of Mikania laevigata. Planta Med. 2016 Nov;82(16):1431-1437. Epub 2016 Jun 23. PubMed PMID: 27336315.

6: Moreira MR, Souza AB, Soares S, Bianchi TC, de Souza Eugênio D, Lemes DC, Martins CH, da Silva Moraes T, Tavares DC, Ferreira NH, Ambrósio SR, Veneziani RC. ent-Kaurenoic acid-rich extract from Mikania glomerata: In vitro activity against bacteria responsible for dental caries. Fitoterapia. 2016 Jul;112:211-6. doi: 10.1016/j.fitote.2016.06.007. Epub 2016 Jun 15. PubMed PMID: 27316976.

7: Okoye TC, Akah PA, Omeje EO, Okoye FB, Nworu CS. Anticonvulsant effect of kaurenoic acid isolated from the root bark of Annona senegalensis. Pharmacol Biochem Behav. 2013 Aug;109:38-43. doi: 10.1016/j.pbb.2013.05.001. Epub 2013 May 8. PubMed PMID: 23664900.

8: de Andrade BB, Moreira MR, Ambrosio SR, Furtado NA, Cunha WR, Heleno VC, Silva AN, Simão MR, da Rocha EM, Martins CH, Veneziani RC. Evaluation of ent-kaurenoic acid derivatives for their anticariogenic activity. Nat Prod Commun. 2011 Jun;6(6):777-80. PubMed PMID: 21815409.

9: Haraguchi SK, Silva AA, Vidotti GJ, dos Santos PV, Garcia FP, Pedroso RB, Nakamura CV, de Oliveira CM, da Silva CC. Antitrypanasomal activity of novel benzaldehyde-thiosemicarbazone derivatives from kaurenoic acid. Molecules. 2011 Jan 26;16(2):1166-80. doi: 10.3390/molecules16021166. PubMed PMID: 21270733.

10: Mizokami SS, Arakawa NS, Ambrosio SR, Zarpelon AC, Casagrande R, Cunha TM, Ferreira SH, Cunha FQ, Verri WA Jr. Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway. J Nat Prod. 2012 May 25;75(5):896-904. doi: 10.1021/np200989t. Epub 2012 May 10. PubMed PMID: 22574649.

11: Jeong SI, Kim BS, Keum KS, Lee KH, Kang SY, Park BI, Lee YR, You YO. Kaurenoic Acid from Aralia continentalis Inhibits Biofilm Formation of Streptococcus mutans. Evid Based Complement Alternat Med. 2013;2013:160592. doi: 10.1155/2013/160592. Epub 2013 Apr 4. PubMed PMID: 23662113; PubMed Central PMCID: PMC3638610.

12: Choi RJ, Shin EM, Jung HA, Choi JS, Kim YS. Inhibitory effects of kaurenoic acid from Aralia continentalis on LPS-induced inflammatory response in RAW264.7 macrophages. Phytomedicine. 2011 Jun 15;18(8-9):677-82. doi: 10.1016/j.phymed.2010.11.010. Epub 2011 Jan 5. PubMed PMID: 21211951.

13: Fernandes VC, Pereira SI, Coppede J, Martins JS, Rizo WF, Beleboni RO, Marins M, Pereira PS, Pereira AM, Fachin AL. The epimer of kaurenoic acid from Croton antisyphiliticus is cytotoxic toward B-16 and HeLa tumor cells through apoptosis induction. Genet Mol Res. 2013 Apr 2;12(2):1005-11. doi: 10.4238/2013.April.2.16. PubMed PMID: 23613246.

14: Yang Y, Chen K. Molecular evolution of the ent-kaurenoic acid oxidase gene in Oryzeae. Genet Mol Biol. 2012 Apr;35(2):448-54. doi: 10.1590/S1415-47572012005000020. Epub 2012 Feb 16. PubMed PMID: 22888294; PubMed Central PMCID: PMC3389533.

15: Gasparetto JC, de Francisco TM, Campos FR, Pontarolo R. Development and validation of two methods based on high-performance liquid chromatography-tandem mass spectrometry for determining 1,2-benzopyrone, dihydrocoumarin, o-coumaric acid, syringaldehyde and kaurenoic acid in guaco extracts and pharmaceutical preparations. J Sep Sci. 2011 Apr;34(7):740-8. doi: 10.1002/jssc.201000792. Epub 2011 Mar 4. PubMed PMID: 21374810.

16: Paiva LA, Gurgel LA, Silva RM, Tomé AR, Gramosa NV, Silveira ER, Santos FA, Rao VS. Anti-inflammatory effect of kaurenoic acid, a diterpene from Copaifera langsdorffi on acetic acid-induced colitis in rats. Vascul Pharmacol. 2002 Dec;39(6):303-7. PubMed PMID: 14567068.

17: Guillopé R, Escobar-Khondiker M, Guérineau V, Laprévote O, Höglinger GU, Champy P. Kaurenoic acid from pulp of Annona cherimolia in regard to Annonaceae-induced Parkinsonism. Phytother Res. 2011 Dec;25(12):1861-4. doi: 10.1002/ptr.3508. Epub 2011 Apr 25. PubMed PMID: 21520310.

18: Fucina G, Block LC, Baccarin T, Ribeiro TR, Quintão NL, Filho VC, Silva RM, Bresolin TM. Development and validation of a stability indicative HPLC-PDA method for kaurenoic acid in spray dried extracts of Sphagneticola trilobata (L.) Pruski, Asteraceae. Talanta. 2012 Nov 15;101:530-6. doi: 10.1016/j.talanta.2012.09.024. Epub 2012 Sep 25. PubMed PMID: 23158359.

19: Cavalcanti BC, Ferreira JR, Moura DJ, Rosa RM, Furtado GV, Burbano RR, Silveira ER, Lima MA, Camara CA, Saffi J, Henriques JA, Rao VS, Costa-Lotufo LV, Moraes MO, Pessoa C. Structure-mutagenicity relationship of kaurenoic acid from Xylopia sericeae (Annonaceae). Mutat Res. 2010 Aug 30;701(2):153-63. doi: 10.1016/j.mrgentox.2010.06.010. Epub 2010 Jun 25. PubMed PMID: 20599626.

20: Fambrini M, Mariotti L, Parlanti S, Picciarelli P, Salvini M, Ceccarelli N, Pugliesi C. The extreme dwarf phenotype of the GA-sensitive mutant of sunflower, dwarf2, is generated by a deletion in the ent-kaurenoic acid oxidase1 (HaKAO1) gene sequence. Plant Mol Biol. 2011 Mar;75(4-5):431-50. doi: 10.1007/s11103-011-9740-x. Epub 2011 Feb 1. PubMed PMID: 21279813.