Synonym
Chaparrin; NSC 79404; NSC 79404; NSC 79404
IUPAC/Chemical Name
Picras-3-en-16-one, 11,20-epoxy-1,2,11,12-tetrahydroxy-, (1beta,2alpha,11beta,12alpha)-
InChi Key
SYRCAVSNPCUQCQ-ZKNGBWAJSA-N
InChi Code
InChI=1S/C20H28O7/c1-8-4-12(21)16(24)18(3)10(8)5-13-19-7-26-20(25,17(18)19)15(23)9(2)11(19)6-14(22)27-13/h4,9-13,15-17,21,23-25H,5-7H2,1-3H3/t9-,10+,11+,12+,13-,15-,16-,17-,18-,19-,20+/m1/s1
SMILES Code
CC([C@](C[C@@](O1)2[H])3[H])=C[C@H](O)[C@@H](O)[C@]3(C)[C@]4([H])[C@]2(CO[C@@]4(O)[C@H](O)[C@@H]5C)[C@@]5([H])CC1=O
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
380.44
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: Calzado-Flores C, Segura-Luna JJ. In vitro cytotoxicity of chaparrin from Castela texana. Proc West Pharmacol Soc. 1995;38:49-50. PMID: 7480018.
2: Ekong RM, Kirby GC, Patel G, Phillipson JD, Warhurst DC. Comparison of the in vitro activities of quassinoids with activity against Plasmodium falciparum, anisomycin and some other inhibitors of eukaryotic protein synthesis. Biochem Pharmacol. 1990 Jul 15;40(2):297-301. doi: 10.1016/0006-2952(90)90691-d. PMID: 2198027.
3: Kirby GC, O'Neill MJ, Phillipson JD, Warhurst DC. In vitro studies on the mode of action of quassinoids with activity against chloroquine-resistant Plasmodium falciparum. Biochem Pharmacol. 1989 Dec 15;38(24):4367-74. doi: 10.1016/0006-2952(89)90644-8. PMID: 2690830.
4: Ozeki A, Hitotsuyanagi Y, Hashimoto E, Itokawa H, Takeya K, de Mello Alves S. Cytotoxic quassinoids from Simaba cedron. J Nat Prod. 1998 Jun 26;61(6):776-80. doi: 10.1021/np980023f. PMID: 9644063.
5: Dou J, McChesney JD, Sindelar RD, Goins DK, Walker LA. A new quassinoid from Castela texana. J Nat Prod. 1996 Jan;59(1):73-6. doi: 10.1021/np960013j. PMID: 8984156.
6: Calzado-Flores C, Segura-Luna JJ, Guajardo-Touche EM. Effects of chaparrin, nordihydroguaiaretic acid and their structural analogues on Entamoeba histolytica cultures. Proc West Pharmacol Soc. 1995;38:105-6. PMID: 7479999.
7: Zhang M, Chaudhuri SK, Kubo I. Quantification of insect growth and its use in screening of naturally occurring insect control agents. J Chem Ecol. 1993 Jun;19(6):1109-18. doi: 10.1007/BF00987372. PMID: 24249129.
8: Calzado-Flores C, Guajardo-Touche EM, Carranza-Rosales MP, Segura-Luna JJ. In vitro anti-trichomonic activity of Castela texana. Proc West Pharmacol Soc. 1998;41:173-4. PMID: 9836284.
9: Calzado-Flores CC, Segura-Luna JJ, Domínguez XA, García-González S. Castela texana: cernimiento de su actividad antiamibiana [Castela texana: screening for its anti-amoebic activity]. Arch Invest Med (Mex). 1986;17 Suppl 1:127-34. Spanish. PMID: 2884948.
