Synonym
Scopadulciol; Dulcinol
IUPAC/Chemical Name
9,11a-Methano-11aH-cyclohepta(a)naphthalen-8(9H)-one, 5-(benzoyloxy)dodecahydro-4-(hydroxymethyl)-4,9,11b-trimethyl-, (4R-(4alpha,4aalpha,5beta,6abeta,9beta,11abeta,11bbeta))-
InChi Key
CFPMRJFTBKYCRR-FOOPCEIZSA-N
InChi Code
InChI=1S/C27H36O4/c1-24-12-13-27(16-24)19(15-21(24)29)14-20(31-23(30)18-8-5-4-6-9-18)22-25(2,17-28)10-7-11-26(22,27)3/h4-6,8-9,19-20,22,28H,7,10-17H2,1-3H3/t19-,20+,22-,24-,25-,26-,27-/m0/s1
SMILES Code
O=C([C@@](C1)(C)CC2)C[C@@]3([H])[C@]21[C@@]4(C)CCC[C@@](C)(CO)[C@]4([H])[C@H](OC(C5=CC=CC=C5)=O)C3
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
424.58
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: Fuentes RG, Toume K, Arai MA, Sadhu SK, Ahmed F, Ishibashi M. Scopadulciol, Isolated from Scoparia dulcis, Induces β-Catenin Degradation and Overcomes Tumor Necrosis Factor-Related Apoptosis Ligand Resistance in AGS Human Gastric Adenocarcinoma Cells. J Nat Prod. 2015 Apr 24;78(4):864-72. doi: 10.1021/np500933v. Epub 2015 Mar 20. PMID: 25793965.
2: Hayashi T, Asano S, Mizutani M, Takeguchi N, Kojima T, Okamura K, Morita N. Scopadulciol, an inhibitor of gastric H+, K(+)-ATPase from Scoparia dulcis, and its structure-activity relationships. J Nat Prod. 1991 May-Jun;54(3):802-9. doi: 10.1021/np50075a008. PMID: 1659612.
3: Hayashi K, Lee JB, Maitani Y, Toyooka N, Nemoto H, Hayashi T. The role of a HSV thymidine kinase stimulating substance, scopadulciol, in improving the efficacy of cancer gene therapy. J Gene Med. 2006 Aug;8(8):1056-67. doi: 10.1002/jgm.931. PMID: 16779868.
4: Hayashi T. [Investigation on traditional medicines of Guarany Indio and studies on diterpenes from Scoparia dulcis]. Yakugaku Zasshi. 2011;131(9):1259-69. Japanese. doi: 10.1248/yakushi.131.1259. PMID: 21881299.
5: Ahsan M, Islam SK, Gray AI, Stimson WH. Cytotoxic diterpenes from Scoparia dulcis. J Nat Prod. 2003 Jul;66(7):958-61. doi: 10.1021/np020356j. PMID: 12880314.
6: Hayashi T. [Studies on evaluation of natural products for antiviral effects and their applications]. Yakugaku Zasshi. 2008 Jan;128(1):61-79. Japanese. doi: 10.1248/yakushi.128.61. PMID: 18176057.
7: Hayashi K, Rahman SM, Ohno H, Tanaka T, Toyooka N, Nemoto H, Hayashi T. Evaluation of scopadulciol-related molecules for their stimulatory effect on the cytotoxicity of acyclovir and ganciclovir against Herpes simplex virus type 1 thymidine kinase gene-transfected HeLa cells. Chem Pharm Bull (Tokyo). 2004 Aug;52(8):1015-7. doi: 10.1248/cpb.52.1015. PMID: 15305006.
8: Liu Q, Yang QM, Hu HJ, Yang L, Yang YB, Chou GX, Wang ZT. Bioactive diterpenoids and flavonoids from the aerial parts of Scoparia dulcis. J Nat Prod. 2014 Jul 25;77(7):1594-600. doi: 10.1021/np500150f. Epub 2014 Jun 23. PMID: 24955889.
