Synonym
Oxacyclododecindione
IUPAC/Chemical Name
(E)-14-chloro-5,11,13-trihydroxy-4,5,9-trimethyl-4,5,6,7-tetrahydro-2H-benzo[d][1]oxacyclododecine-2,10(1H)-dione
InChi Key
CKSXTSLBLCBNFG-WEVVVXLNSA-N
InChi Code
InChI=1S/C18H21ClO6/c1-9-5-4-6-18(3,24)10(2)25-14(22)7-11-15(17(9)23)12(20)8-13(21)16(11)19/h5,8,10,20-21,24H,4,6-7H2,1-3H3/b9-5+
SMILES Code
O=C(CC1=C(Cl)C(O)=CC(O)=C12)OC(C)C(C)(O)CC/C=C(C)/C2=O
Appearance
To be determined
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
368.81
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. Erkel G, Belahmer H, Serwe A, Anke T, Kunz H, Kolshorn H, Liermann J, Opatz T. Oxacyclododecindione, a novel inhibitor of IL-4 signaling from Exserohilum rostratum. J Antibiot (Tokyo). 2008 May;61(5):285-90. doi: 10.1038/ja.2008.40. PMID: 18653993.
2. Tauber J, Rohr M, Walter T, Erkel G, Opatz T. Total synthesis of two potent anti-inflammatory macrolactones of the oxacyclododecindione type. Org Biomol Chem. 2015 Jul 28;13(28):7813-21. doi: 10.1039/c5ob01044f. Epub 2015 Jun 24. Erratum in: Org Biomol Chem. 2015 Sep 7;13(33):8945-6. PMID: 26106910.
3. Henke J, Erkel G, Brochhausen C, Kleinert H, Schwarting A, Menke J, Pautz A. The fungal lactone oxacyclododecindione is a potential new therapeutic substance in the treatment of lupus-associated kidney disease. Kidney Int. 2014 Oct;86(4):780-9. doi: 10.1038/ki.2014.109. Epub 2014 Apr 9. PMID: 24717299.