Grandiflorenic acid | CAS#22338-67-6 | antifertility

MedKoo Cat#: 558139 | Name: Grandiflorenic acid

Description:

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

Grandiflorenic acid can reproduce the uterine responses induced by aqueous extract of zoapatle leaves, suggests that grandiflorenic acid may have antifertility effect.

Chemical Structure

Grandiflorenic acid

CAS#22338-67-6

Theoretical Analysis

MedKoo Cat#: 558139

Name: Grandiflorenic acid

CAS#: 22338-67-6

Chemical Formula: C20H28O2

Exact Mass: 300.2100

Molecular Weight: 300.44

Elemental Analysis: C, 79.96; H, 9.39; O, 10.65

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

IUPAC/Chemical Name

Kaura-9(11),16-dien-18-oic acid

InChi Key

RJIPNPHMQGDUBW-RFGKEDTNSA-N

InChi Code

InChI=1S/C20H28O2/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/h6,14-15H,1,4-5,7-12H2,2-3H3,(H,21,22)/t14-,15+,18-,19-,20-/m1/s1

SMILES Code

C=C1C[C@@]23CC[C@]4([H])[C@@](C(O)=O)(C)CCC[C@@]4(C)C2=CC[C@@H]1C3

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 300.44 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.

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

1: Ruan Y, Ma BJ, Li LZ, Wang XL. Specific 12α-hydroxylation of grandiflorenic acid by permeabilised fungus Fusarium graminearum. Nat Prod Res. 2014;28(9):677-9. doi: 10.1080/14786419.2014.891113. Epub 2014 Mar 21. PubMed PMID: 24650196. 2: Neidlein R, Stumpf U. [Biotransformation and pharmacokinetics of grandiflorenic acid [kauradiene-9(11),16-oic acid-18] / 1st communication (author's transl)]. Arzneimittelforschung. 1977;27(5):999-1004. German. PubMed PMID: 577885. 3: Neidlein R, Stumpf U. [Biotransformation and pharmacokinetics of grandiflorenic acid [kauradien-9(11),16-oic acid-18] / 2nd communication (author's transl)]. Arzneimittelforschung. 1977;27(6):1162-6. German. PubMed PMID: 578433. 4: Neidlein R, Stumpf U. [Biotransformation and pharmacokinetics of grandiflorenic acid [kauradien-9(11),16-oic acid-18]. 3rd communication (author's transl)]. Arzneimittelforschung. 1977 Jul;27(7):1384-90. German. PubMed PMID: 578458. 5: Bejar E, Enriquez R, Lozoya X. The in vitro effect of grandiflorenic acid and zoapatle aqueous crude extract upon spontaneous contractility of the rat uterus during oestrus cycle. J Ethnopharmacol. 1984 Jun;11(1):87-97. PubMed PMID: 6540830. 6: Bejar E. Preliminary investigation of the estrogenic potential of grandiflorenic acid from Montanoa tomentosa. J Ethnopharmacol. 1988 Jul-Aug;23(2-3):329-31. PubMed PMID: 3193796. 7: Fraga BM, Cabrera I, Amaro-Luis JM. On the structures of the diterpenes licamichauxiioic acids A and B. J Nat Prod. 2008 Nov;71(11):1953-5. doi: 10.1021/np800370f. Epub 2008 Oct 11. PubMed PMID: 18847245. 8: Fraga BM, González-Vallejo V, Guillermo R, Amaro-Luis JM. Microbiological transformation of two 15α-hydroxy-ent-kaur-9(11),16-diene derivatives by the fungus Fusarium fujikuroi. Phytochemistry. 2013 May;89:39-46. doi: 10.1016/j.phytochem.2013.01.006. Epub 2013 Feb 8. PubMed PMID: 23398890. 9: Villa-Ruano N, Betancourt-Jiménez MG, Lozoya-Gloria E. Biosynthesis of uterotonic diterpenes from Montanoa tomentosa (zoapatle). J Plant Physiol. 2009 Dec 15;166(18):1961-7. doi: 10.1016/j.jplph.2009.06.004. Epub 2009 Jul 5. PubMed PMID: 19581023. 10: Robles-Zepeda RE, Lozoya-Gloria E, López MG, Villarreal ML, Ramírez-Chávez E, Molina-Torres J. Montanoa tomentosa glandular trichomes containing kaurenoic acids chemical profile and distribution. Fitoterapia. 2009 Jan;80(1):12-7. doi: 10.1016/j.fitote.2008.09.002. Epub 2008 Sep 14. PubMed PMID: 18824221. 11: Boaventura MA, Pereira RG, de Oliveira Freitas LB, Dos Reis LA, da Silva Vieira H. Preparation and phytotoxicity of novel kaurane diterpene amides with potential use as herbicides. J Agric Food Chem. 2008 May 14;56(9):2985-8. doi: 10.1021/jf0729309. Epub 2008 Apr 5. PubMed PMID: 18393433. 12: Page JE, Balza F, Nishida T, Towers GH. Biologically active diterpenes from Aspilia mossambicensis, a chimpanzee medicinal plant. Phytochemistry. 1992 Oct;31(10):3437-9. PubMed PMID: 1368857. 13: Vieira HS, Takahashi JA, Gunatilaka AA, Boaventura MA. 1H and 13C NMR signal assignments of a novel Baeyer-Villiger originated diterpene lactone. Magn Reson Chem. 2006 Feb;44(2):146-50. PubMed PMID: 16358289. 14: Lozoya X, Enríquez RG, Bejar E, Estrada AV, Girón H, Ponce-Monter H, Gallegos AJ. The zoapatle V--the effect of kauradienoic acid upon uterine contractility. Contraception. 1983 Mar;27(3):267-79. PubMed PMID: 6851560. 15: Hueso-Falcón I, Girón N, Velasco P, Amaro-Luis JM, Ravelo AG, de las Heras B, Hortelano S, Estevez-Braun A. Synthesis and induction of apoptosis signaling pathway of ent-kaurane derivatives. Bioorg Med Chem. 2010 Feb 15;18(4):1724-35. doi: 10.1016/j.bmc.2009.11.064. Epub 2009 Dec 6. PubMed PMID: 20116261. 16: Lebrasseur N, Gagnepain J, Ozanne-Beaudenon A, Léger JM, Quideau S. Efficient access to orthoquinols and their [4 + 2] cyclodimers via SIBX-mediated hydroxylative phenol dearomatization. J Org Chem. 2007 Aug 3;72(16):6280-3. Epub 2007 Jul 12. PubMed PMID: 17628111. 17: Vieira HS, Takahashi JA, Pimenta LP, Boaventura MA. Effects of kaurane diterpene derivatives on germination and growth of Lactuca sativa seedlings. Z Naturforsch C. 2005 Jan-Feb;60(1-2):72-8. PubMed PMID: 15787248. 18: Béjar E, Lozoya X, Enríquez R, Escobar L. Comparative effect of zoapatle (Montanoa tomentosa) products and of verapamil on the in vitro uterine contractility of rat. Arch Invest Med (Mex). 1984 Jul-Sep;15(3):223-38. English, Spanish. PubMed PMID: 6598740. 19: Pereira RG, Cala A, Fernández-Aparicio M, Molinillo JM, Boaventura MA, Macías FA. Gibberellic and kaurenoic hybrid strigolactone mimics for seed germination of parasitic weeds. Pest Manag Sci. 2017 Dec;73(12):2529-2537. doi: 10.1002/ps.4650. Epub 2017 Aug 18. PubMed PMID: 28643859. 20: Arciniegas A, Pérez-Castorena AL, Meléndez-Aguirre M, Ávila JG, García-Bores AM, Villaseñor JL, Romo de Vivar A. Chemical Composition and Antimicrobial Activity of Ageratina deltoidea. Chem Biodivers. 2018 Mar;15(3):e1700529. doi: 10.1002/cbdv.201700529. PubMed PMID: 29427474.