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Acremolactone A

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Category Others
Catalog number BBF-00015
CAS
Molecular Weight 474.54
Molecular Formula C26H34O8

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

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Acremolactone A, a novel herbicidal epoxydihydropyranyl gamma-lactone from Acremonium roseum I4267.

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IUPAC Name 7-hydroxy-3-[(E)-1-hydroxy-2-methylhex-2-enyl]-12-(2-hydroxy-6-methyl-7-oxabicyclo[4.1.0]hept-3-en-1-yl)-6-methyl-5,11,13-trioxatetracyclo[7.5.0.02,6.010,12]tetradec-1(14)-en-4-one
Canonical SMILES CCCC=C(C)C(C1C2C3=COC4(C(C3CC(C2(OC1=O)C)O)O4)C56C(C=CCC5(O6)C)O)O
InChI InChI=1S/C26H34O8/c1-5-6-8-13(2)20(29)18-19-15-12-31-26(25-16(27)9-7-10-23(25,3)34-25)21(32-26)14(15)11-17(28)24(19,4)33-22(18)30/h7-9,12,14,16-21,27-29H,5-6,10-11H2,1-4H3/b13-8+
InChI Key AIDBYRCMBCUHKZ-MDWZMJQESA-N
Appearance Colorless Crystal
Melting Point 123.5-124°C
1. Isolation and structures of acremolactones B and C, novel plant-growth inhibitory gamma-lactones from Acremonium roseum I4267
Takeshi Sassa, Takahiro Ooi, Hiroshi Kinoshita Biosci Biotechnol Biochem. 2004 Dec;68(12):2633-6. doi: 10.1271/bbb.68.2633.
Novel acremolactones B and C were isolated from the acremolactone A-producing Acremonium roseum I4267. The structure of acremolactone B having a phenylpyridyl gamma-lactone was elucidated by spectroscopic methods. It showed plant growth inhibitory activity toward Chinese cabbage seedlings. The congener of acremolactone C having a phenylcyclopentenone gamma-lactone showed weak activity.
2. Absolute stereochemistry of acremolactone A, a novel herbicidal epoxydihydropyranyl gamma-lactone from Acremonium roseum I4267
Takeshi Sassa, Takahiro Ooi, Hiroshi Kinoshita, Katsuhide Okada Biosci Biotechnol Biochem. 2004 Oct;68(10):2201-4. doi: 10.1271/bbb.68.2201.
Acremolactone A was chemically degraded to the bicyclic hemiacetal gamma-lactone and an epoxycyclohexenol, and their stereochemistry was determined by spectroscopic methods. These observations and data from NOE experiments on acremolactone A led to the configurational assignment of all asymmetric carbons in acremolactone A, enabling its stereostructure to be established.

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