Related CAS #
10092-04-3 (isotenulin); 19202-92-7 (tenulin)
Synonym
NSC 85247; NSC-085247; NSC85247;
IUPAC/Chemical Name
(3R,3aR,4R,4aR,8R,9aS)-3,4a,8-trimethyl-2,5-dioxo-2,3,3a,4,4a,5,7a,8,9,9a-decahydroazuleno[6,5-b]furan-4-yl acetate
InChi Key
NEIIKBWBBCJSQU-DGIONXRUSA-N
InChi Code
InChI=1S/C17H22O5/c1-8-7-12-14(9(2)16(20)22-12)15(21-10(3)18)17(4)11(8)5-6-13(17)19/h5-6,8-9,11-12,14-15H,7H2,1-4H3/t8-,9-,11?,12+,14-,15-,17+/m1/s1
SMILES Code
C[C@@H]1C[C@@H]2OC([C@@H]([C@H]2[C@H]([C@]3(C1C=CC3=O)C)OC(C)=O)C)=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
>3 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
306.36
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: Chang YT, Wang CCN, Wang JY, Lee TE, Cheng YY, Morris-Natschke SL, Lee KH, Hung CC. Tenulin and isotenulin inhibit P-glycoprotein function and overcome multidrug resistance in cancer cells. Phytomedicine. 2019 Feb;53:252-262. doi: 10.1016/j.phymed.2018.09.008. Epub 2018 Sep 5. PMID: 30668405; PMCID: PMC6421864.
2: Knight KS, Smith CT, Waddell TG. Isotenulin. Acta Crystallogr Sect E Struct Rep Online. 2013 Jul 20;69(Pt 8):o1290. doi: 10.1107/S1600536813019703. PMID: 24109370; PMCID: PMC3793783.
3: ElSohly Ma, Kulanthaivel P, Herz W. Constituents of Helenium amarum, IV. Desacetyl-1-epiisotenulin. J Nat Prod. 1984 May-Jun;47(3):533-5. doi: 10.1021/np50033a024. PMID: 6548253.
4: Waddell TG, Austin AM, Cochran JW, Gerhart KG, Hall IH, Lee KH. Antitumor agents: structure--activity relationships in tenulin series. J Pharm Sci. 1979 Jun;68(6):715-8. doi: 10.1002/jps.2600680616. PMID: 458570.
