MedKoo Cat#: 112011 | Name: Gypsogenic Acid
Featured

Description:

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

Gypsogenic acid is a triterpene acid that has been found in M. stenostachya and has antibacterial and trypanocidal activities. It is active against the oral bacterial pathogens E. faecalis, S. salivarius, S. sanguinis, S. mitis, S. mutans, and S. sobrinus (MICs = 50-200 µg/ml). Gypsogenic acid induces lysis of T. cruzi in isolated mouse blood (IC50 = 56.6 µM).

Chemical Structure

Gypsogenic Acid
Gypsogenic Acid
CAS#5143-05-5

Theoretical Analysis

MedKoo Cat#: 112011

Name: Gypsogenic Acid

CAS#: 5143-05-5

Chemical Formula: C30H46O5

Exact Mass: 486.3345

Molecular Weight: 486.69

Elemental Analysis: C, 74.04; H, 9.53; O, 16.44

Price and Availability

Size Price Availability Quantity
2.5mg USD 550.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Gypsogenic Acid; Gypsogeninic acid; Astrantiagenin J; Acanjapogenin G;
IUPAC/Chemical Name
(3S,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-3-hydroxy-4,6a,6b,11,11,14b-hexamethyl-2,3,4,4a,5,6,6a,6b,7,8,9,10,11,12,12a,14,14a,14b-octadecahydropicene-4,8a(1H)-dicarboxylic acid
InChi Key
PAIBKVQNJKUVCE-JUENUIDLSA-N
InChi Code
InChI=1S/C30H46O5/c1-25(2)13-15-30(24(34)35)16-14-27(4)18(19(30)17-25)7-8-20-26(3)11-10-22(31)29(6,23(32)33)21(26)9-12-28(20,27)5/h7,19-22,31H,8-17H2,1-6H3,(H,32,33)(H,34,35)/t19-,20+,21+,22-,26+,27+,28+,29-,30-/m0/s1
SMILES Code
CC1(C)CC[C@]2(C(O)=O)CC[C@@]3(C)[C@]4(C)CC[C@@]5([H])[C@](C)(C(O)=O)[C@@H](O)CC[C@]5(C)[C@@]4([H])CC=C3[C@]2([H])C1
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 486.69 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
1: Hammami A, Farman M, Semmar N. Highlighting Aglycone-dependent Glycosylation Aspects in Caryophyllaceae Saponins by a Simplex Simulation Approach. Curr Top Med Chem. 2021;21(7):612-627. doi: 10.2174/1568026621666210114153216. PMID: 33459236. 2: Usmanov D, Yusupova U, Syrov V, Ramazonov N, Rasulev B. Iridoid glucosides and triterpene acids from Phlomis linearifolia, growing in Uzbekistan and its hepatoprotective activity. Nat Prod Res. 2021 Jul;35(14):2449-2453. doi: 10.1080/14786419.2019.1677650. Epub 2019 Oct 24. PMID: 31646905. 3: Kim YB, Reed DW, Covello PS. Production of Triterpenoid Sapogenins in Hairy Root Cultures of Silene vulgaris. Nat Prod Commun. 2015 Nov;10(11):1919-22. PMID: 26749827. 4: Xie LX, Zhang HC, Wang HY, Wang Y, Wang FL, Sun JY. Two new triterpenoids from Gypsophila oldhamiana. Nat Prod Res. 2016;30(9):1068-74. doi: 10.1080/14786419.2015.1107060. Epub 2015 Nov 5. PMID: 26539898. 5: Seo JH, Kim MO, Han AR, Kwon EB, Kang MJ, Cho S, Moon DO, Noh JR, Lee CH, Kim YS, Lee HS. Oleanane-type triterpenoids of Aceriphyllum rossii and their diacylglycerol acyltransferase-inhibitory activity. Planta Med. 2015 Feb;81(3):228-34. doi: 10.1055/s-0034-1396242. Epub 2015 Feb 11. PMID: 25671385. 6: Wang J, Ren H, Xu QL, Zhou ZY, Wu P, Wei XY, Cao Y, Chen XX, Tan JW. Antibacterial oleanane-type triterpenoids from pericarps of Akebia trifoliata. Food Chem. 2015 Feb 1;168:623-9. doi: 10.1016/j.foodchem.2014.07.105. Epub 2014 Jul 31. PMID: 25172756. 7: Krasteva I, Yotova M, Yosifov D, Benbassat N, Jenett-Siems K, Konstantinov S. Cytotoxicity of gypsogenic acid isolated from Gypsophila trichotoma. Pharmacogn Mag. 2014 Apr;10(Suppl 2):S430-3. doi: 10.4103/0973-1296.133299. PMID: 24991123; PMCID: PMC4078331. 8: Pertuit D, Avunduk S, Mitaine-Offer AC, Miyamoto T, Tanaka C, Paululat T, Delemasure S, Dutartre P, Lacaille-Dubois MA. Triterpenoid saponins from the roots of two Gypsophila species. Phytochemistry. 2014 Jun;102:182-8. doi: 10.1016/j.phytochem.2014.02.018. Epub 2014 Apr 8. PMID: 24725976. 9: Moniuszko-Szajwaj B, Pecio L, Kowalczyk M, Simonet AM, Macias FA, Szumacher- Strabel M, Cieslak A, Oleszek W, Stochmal A. New triterpenoid saponins from the roots of Saponaria officinalis. Nat Prod Commun. 2013 Dec;8(12):1687-90. PMID: 24555273. 10: Fukushima EO, Seki H, Sawai S, Suzuki M, Ohyama K, Saito K, Muranaka T. Combinatorial biosynthesis of legume natural and rare triterpenoids in engineered yeast. Plant Cell Physiol. 2013 May;54(5):740-9. doi: 10.1093/pcp/pct015. Epub 2013 Jan 31. PMID: 23378447. 11: Luo JG, Chen X, Kong LY. Three new triterpenoid saponins from Dianthus superbus. Chem Pharm Bull (Tokyo). 2011;59(4):518-21. doi: 10.1248/cpb.59.518. PMID: 21467688. 12: Timité G, Mitaine-Offer AC, Miyamoto T, Ramezani M, Rustaiyan A, Mirjolet JF, Duchamp O, Lacaille-Dubois MA. Structure elucidation of new oleanane-type glycosides from three species of Acanthophyllum. Magn Reson Chem. 2010 May;48(5):370-4. doi: 10.1002/mrc.2577. PMID: 20209583. 13: Huang W, Li Y, Jiang J. [Chemical constituents from Hedyotis diffusa]. Zhongguo Zhong Yao Za Zhi. 2009 Mar;34(6):712-4. Chinese. PMID: 19624011. 14: Scalon Cunha LC, Andrade e Silva ML, Cardoso Furtado NA, Vinhólis AH, Martins CH, da Silva Filho AA, Cunha WR. Antibacterial activity of triterpene acids and semi-synthetic derivatives against oral pathogens. Z Naturforsch C J Biosci. 2007 Sep-Oct;62(9-10):668-72. doi: 10.1515/znc-2007-9-1007. PMID: 18069238. 15: Lee I, Yoo JK, Na M, Min BS, Lee J, Yun BS, Jin W, Kim H, Youn U, Chen QC, Song KS, Seong YH, Bae K. Cytotoxicity of triterpenes isolated from Aceriphyllum rossii. Chem Pharm Bull (Tokyo). 2007 Sep;55(9):1376-8. doi: 10.1248/cpb.55.1376. PMID: 17827765. 16: Zheng Q, Li W, Han L, Koike K. Pancreatic lipase-inhibiting triterpenoid saponins from Gypsophila oldhamiana. Chem Pharm Bull (Tokyo). 2007 Apr;55(4):646-50. doi: 10.1248/cpb.55.646. PMID: 17409564. 17: Alabdul Magid A, Voutquenne L, Moretti C, Long C, Lavaud C. Triterpenoid saponins from the fruits of Caryocar glabrum. J Nat Prod. 2006 Feb;69(2):196-205. doi: 10.1021/np050336s. PMID: 16499316. 18: Park SY, Yook CS, Nohara T. New oleanene glycosides from the leaves of Acanthopanax japonicus. Chem Pharm Bull (Tokyo). 2005 Sep;53(9):1147-51. doi: 10.1248/cpb.53.1147. PMID: 16141585. 19: Gaidi G, Miyamoto T, Lacaille-Dubois MA. An unusual new sulfated triterpene saponin from Arenaria juncea. Pharmazie. 2005 Aug;60(8):635-7. PMID: 16124413. 20: Cunha WR, Martins C, da Silva Ferreira D, Crotti AE, Lopes NP, Albuquerque S. In vitro trypanocidal activity of triterpenes from miconia species. Planta Med. 2003 May;69(5):470-2. doi: 10.1055/s-2003-39719. PMID: 12802734.