IUPAC/Chemical Name
(3S)-8-hydroxy-3-methyl-3,4-dihydro-2H-benzo[a]anthracene-1,7,12-trione
InChi Key
ZAWXOCUFQSQDJS-VIFPVBQESA-N
InChi Code
InChI=1S/C19H14O4/c1-9-7-10-5-6-12-17(15(10)14(21)8-9)19(23)11-3-2-4-13(20)16(11)18(12)22/h2-6,9,20H,7-8H2,1H3/t9-/m0/s1
SMILES Code
CC1CC2=C(C(=O)C1)C3=C(C=C2)C(=O)C4=C(C3=O)C=CC=C4O
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
Biological target:
(+)-Ochromycinone is a natural antibiotic that potently inhibits STAT3.
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
25.0 |
81.61 |
| DMF:PBS (pH 7.2) (1:2) |
0.3 |
0.98 |
| DMSO |
16.0 |
52.23 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
306.32
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 |
Formulation protocol:
TBD
1: Boonlarppradab C, Suriyachadkun C, Rachtawee P, Choowong W. Saccharosporones A, B and C, cytotoxic antimalarial angucyclinones from Saccharopolyspora sp. BCC 21906. J Antibiot (Tokyo). 2013 Jun;66(6):305-9. doi: 10.1038/ja.2013.16. Epub 2013 Apr 3. PMID: 23549355.
2: Sajid I, Shaaban KA, Hasnain S. Purification and identification of bioactive angucyclinones from Streptomyces matensis BG5, isolated from the rhizosphere of Rosa indica L. Prep Biochem Biotechnol. 2013;43(1):22-32. doi: 10.1080/10826068.2012.693897. PMID: 23215652.
3: Abdalla MA, Helmke E, Laatsch H. Fujianmycin C, A bioactive angucyclinone from a marine derived Streptomyces sp. B6219. Nat Prod Commun. 2010 Dec;5(12):1917-20. PMID: 21299120.
4: Fotso S, Mahmud T, Zabriskie TM, Santosa DA, Sulastri, Proteau PJ. Angucyclinones from an Indonesian Streptomyces sp. J Nat Prod. 2008 Jan;71(1):61-5. doi: 10.1021/np0704102. Epub 2007 Dec 15. PMID: 18081255.
5: Kaliappan KP, Ravikumar V. Angucyclinone antibiotics: total syntheses of YM-181741, (+)-ochromycinone, (+)-rubiginone B2, (-)-tetrangomycin, and MM-47755. J Org Chem. 2007 Aug 3;72(16):6116-26. doi: 10.1021/jo070709p. Epub 2007 Jul 11. PMID: 17625884.
6: Yamamoto Y. From sigma- to pi-electrophilic Lewis acids. Application to selective organic transformations. J Org Chem. 2007 Oct 12;72(21):7817-31. doi: 10.1021/jo070579k. Epub 2007 Jun 19. Erratum in: J Org Chem. 2008 Jul 4;73(13):5210. PMID: 17579452.
7: Sato K, Asao N, Yamamoto Y. Efficient method for synthesis of angucyclinone antibiotics via gold-catalyzed intramolecular [4 + 2] benzannulation: enantioselective total synthesis of (+)-ochromycinone and (+)-rubiginone B2. J Org Chem. 2005 Oct 28;70(22):8977-81. doi: 10.1021/jo051444m. PMID: 16238336.
8: Rozek T, Bowie JH, Skelton BW, White AH. 11-Hydroxy-3,3-dimethyl-7,12-dioxo-3 ,4,6,6a,7,12,12a,12b-octahydrobenz[a]anthracen-1-yl acetate. Acta Crystallogr C. 2003 Aug;59(Pt 8):o431-2. doi: 10.1107/s0108270103013374. Epub 2003 Jul 12. PMID: 12909769.
