Synonym
(–)-Acetomycin; NSC 350598; NSC-350598; NSC350598;
IUPAC/Chemical Name
(2R,3S,4S)-4-acetyl-3,4-dimethyl-5-oxotetrahydrofuran-2-yl acetate
InChi Key
OYMZTORLGBISLR-RHFNHBFPSA-N
InChi Code
InChI=1S/C10H14O5/c1-5-8(14-7(3)12)15-9(13)10(5,4)6(2)11/h5,8H,1-4H3/t5-,8-,10+/m1/s1
SMILES Code
C[C@@]1(C(C)=O)[C@H](C)[C@H](OC(C)=O)OC1=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
214.22
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: Mamber SW, Mitulski JD, Borondy PE, Tunac JB. Biological effects of acetomycin. II. Inactivation by esterases in vitro. J Antibiot (Tokyo). 1987 Jan;40(1):77-80. doi: 10.7164/antibiotics.40.77. PMID: 3558119.
2: Mamber SW, Mitulski JD, Hamelehle KL, French JC, Hokanson GC, Shillis JL, Leopold WR, Von Hoff DD, Tunac JB. Biological effects of acetomycin. I. Activity against tumor cells in vitro and in vivo. J Antibiot (Tokyo). 1987 Jan;40(1):73-6. doi: 10.7164/antibiotics.40.73. PMID: 3558118.
3: Calad SA, Woerpel KA. Formation of chiral quaternary carbon stereocenters using silylene transfer reactions: enantioselective synthesis of (+)-5-epi- acetomycin. Org Lett. 2007 Mar 15;9(6):1037-40. doi: 10.1021/ol063072p. Epub 2007 Feb 17. PMID: 17305349.
4: Uenishi J, Kobayashi N, Komine S, Okadai T, Yonemitsu O, Sasaki T, Yamada Y. Total synthesis of (+/-)-acetomycin and design of esterase-resistant analogs. Chem Pharm Bull (Tokyo). 1999 Apr;47(4):517-23. doi: 10.1248/cpb.47.517. PMID: 10319430.
5: Cano FH, Foces-Foces C, Elguero J. The structure and absolute configuration of acetomycin. Acta Crystallogr C. 1988 May 15;44 ( Pt 5):919-21. doi: 10.1107/s0108270188001337. PMID: 3271088.
6: Uhr H, Zeeck A, Clegg W, Egert E, Fuhrer H, Peter HH. The structure of acetomycin. Spectroscopic characterization and X-ray analysis of a bromo derivative. J Antibiot (Tokyo). 1985 Dec;38(12):1684-90. doi: 10.7164/antibiotics.38.1684. PMID: 4093332.
