Synonym
Phytolaccagenin; NSC 116453; NSC-116453; NSC116453; Phytolaccagenine; Jaligonic acid 30-methyl ester;
IUPAC/Chemical Name
(2S,4aR,6aS,6bR,8aR,9R,10R,11S,12aR,12bR,14bS)-10,11-dihydroxy-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid
InChi Key
CYJWWQALTIKOAG-FLORRLIPSA-N
InChi Code
InChI=1S/C31H48O7/c1-26(25(37)38-6)11-13-31(24(35)36)14-12-29(4)18(19(31)15-26)7-8-22-27(2)16-20(33)23(34)28(3,17-32)21(27)9-10-30(22,29)5/h7,19-23,32-34H,8-17H2,1-6H3,(H,35,36)/t19-,20-,21+,22+,23-,26-,27-,28-,29+,30+,31-/m0/s1
SMILES Code
C[C@@]1(CO)[C@@H](O)[C@@H](O)C[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])C[C@@](C)(C(OC)=O)CC[C@@](C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H]
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
532.71
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: Wei F, Singh RS, Fueth M, Swarts S, Okunieff P, Derendorf H. Development and validation of a HPLC-MS/MS method for the determination of phytolaccagenin in rat plasma and application to a pharmacokinetic study. J Pharm Biomed Anal. 2015 Mar 25;107:82-8. doi: 10.1016/j.jpba.2014.12.025. Epub 2014 Dec 22. PubMed PMID: 25575173.
2: Gong W, Jiang Z, Sun P, Li L, Jin Y, Shao L, Zhang W, Liu B, Zhang H, Tang H, Chen Y, Yi Y, Zhang D. Synthesis of novel derivatives of esculentoside A and its aglycone phytolaccagenin, and evaluation of their haemolytic activity and inhibition of lipopolysaccharide-induced nitric oxide production. Chem Biodivers. 2011 Oct;8(10):1833-52. doi: 10.1002/cbdv.201000339. PubMed PMID: 22006712.
3: Di Liberto M, Svetaz L, Furlán RL, Zacchino SA, Delporte C, Novoa MA, Asencio M, Cassels BK. Antifungal activity of saponin-rich extracts of Phytolacca dioica and of the sapogenins obtained through hydrolysis. Nat Prod Commun. 2010 Jul;5(7):1013-8. PubMed PMID: 20734930.
4: Escalante AM, Santecchia CB, López SN, Gattuso MA, Gutiérrez Ravelo A, Delle Monache F, Gonzalez Sierra M, Zacchino SA. Isolation of antifungal saponins from Phytolacca tetramera, an Argentinean species in critic risk. J Ethnopharmacol. 2002 Sep;82(1):29-34. PubMed PMID: 12169402.
5: Spengel SM, Luterbacher S, Schaffner W. New aspects on the chemotaxonomy of Phytolacca dodecandra with regard to the isolation of phytolaccagenin, phytolaccagenic acid and their glycosides. Planta Med. 1995 Aug;61(4):385-6. PubMed PMID: 17238093.
6: Yi YH. Two new saponins from the roots of Phytolacca esculenta. Planta Med. 1992 Feb;58(1):99-101. PubMed PMID: 1620750.
7: Spengel S, Schaffner W. [Acinospesigenin: A New Triterpene from the Leaves of Phytolacca acinosa]. Planta Med. 1990 Jun;56(3):284-6. German. PubMed PMID: 17221419.
8: Yi YH, Wang CL. A new active saponin from Phytolacca esculenta. Planta Med. 1989 Dec;55(6):551-2. PubMed PMID: 2482514.
9: Appel HH, Piovano M, Garbarino JA, Gambaro V. Phytolaccagenic Acid and Phytolaccagenin from Anisomeria coriacea. Planta Med. 1987 Feb;53(1):115. PubMed PMID: 17268985.
