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Category Antibiotics
Catalog number BBF-00540
CAS 510-18-9
Molecular Weight 214.21
Molecular Formula C10H14O5
Purity 98%

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Acetomycin is an anti-human tuberculosis and amoeba antibiotic isolated from the Streptomyces ramnlosus. Acetomycin is an anti-biotic, anti-fungal, anti-protozoal, and anti-bacterial agent


Synonyms (3S,4S,5R)-3-Acetyl-5-(acetyloxy)dihydro-3,4-dimethyl-2(3H)-furanone; (-)-Acetomycin; NSC 350598; [3S-(3α,4α,5α)]-3-acetyl-5-(acetyloxy)dihydro-3,4-dimethyl-2(3H)-furanone
Storage Store at -20°C
IUPAC Name [(2R,3S,4S)-4-acetyl-3,4-dimethyl-5-oxooxolan-2-yl] acetate
Canonical SMILES CC1C(OC(=O)C1(C)C(=O)C)OC(=O)C
InChI 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


Appearance Colorless Needle or Columnar Crystal
Antibiotic Activity Spectrum Neoplastics (Tumor); Fungi; Bacteria
Boiling Point 336.2°C at 760 mmHg
Melting Point 115-116 °C
Density 1.18 g/cm3
Solubility Soluble in DMSO, Methanol

Reference Reading

1. Biological effects of acetomycin. II. Inactivation by esterases in vitro
P E Borondy, J D Mitulski, S W Mamber, J B Tunac J Antibiot (Tokyo) . 1987 Jan;40(1):77-80. doi: 10.7164/antibiotics.40.77.
Acetomycin has antitumor activity in vitro but not in vivo. HCT-8 human colon adenocarcinoma assays in the presence of a drug metabolizing system (rat liver S9 fraction) demonstrated that liver enzymes inactivated acetomycin. The structure of acetomycin suggested that an esterase could be the key inactivating enzyme. Assays with porcine liver esterase (EC showed that this enzyme rapidly abolishes the activity of acetomycin against HCT-8 cells. The potential utility of acetomycin as an antitumor agent thus depends on finding a means of preventing esterase inactivation.
2. Total synthesis of (+/-)-acetomycin and design of esterase-resistant analogs
T Okadai, N Kobayashi, Y Yamada, S Komine, J Uenishi, T Sasaki, O Yonemitsu Chem Pharm Bull (Tokyo) . 1999 Apr;47(4):517-23. doi: 10.1248/cpb.47.517.
The synthesis of acetomycin and related analogs was investigated. Acetomycin was synthesized from diethyl allyl(methyl)malonate in 6.5% yield over 18 steps. The total number of steps was improved compared to our previous synthesis; i.e., four steps shorter, and the total yield was 4.5% greater than the previous synthesis. Acetomycin analogs with benzoyloxy and pivaloyloxy groups, instead of an acetoxy group at the 5-position of the gamma-butyrolactone ring were designed as esterase-resistant models and prepared similarly. Although they showed a similar level of cytotoxicity as acetomycin in vitro, they were not resistant to porcine liver esterase, and lost cytotoxicity in vivo.
3. The structure and absolute configuration of acetomycin
C Foces-Foces, J Elguero, F H Cano Acta Crystallogr C . 1988 May 15;44 ( Pt 5):919-21. doi: 10.1107/s0108270188001337.
C10H14O5, Mr = 214.22, orthorhombic, P2(1)2(1)2(1), a = 14.1084 (6), b = 10.6443 (3), c = 7.1970 (1) A, V = 1080.80 (6) A3, Z = 4, D chi = 1.317 Mg m-3, Cu K alpha, lambda = 1.5418 A, mu = 0.8571 mm-1, F(000) = 456, T = 293 K, R = 0.052 for 816 observed [3 sigma (I)] Friedel pairs. The determined absolute configuration may be described as 3S, 4R, 5R, the five-membered ring having an envelope conformation, with the bulky substituents at cis positions. The bond lengths and angles are in agreement with those of the bromoacetoxy derivative.

Bio Calculators

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40

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