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207319 Palmarumycin C3 CAS: 159934-11-9

Specifications
References
CAS Number
159934-11-9
Grade
Highly Purified
Molecular Formula
C₂₀H₁₂O₆
Molecular Weight
348.3
EU Commodity Code
38220090
UN DOT Shipping
UN3462 PG III Class 6.1
Shipping Temp
RT
Storage Temp
-20°C
(1aR,7aS)-1a,7a-Dihydro-3,6-dihydroxyspiro[naphth[2,3-b]oxirene-2(7H),2’-naphtho[1,8-de][1,3]dioxin]-7-one; (1’aR,7’aS)-1’a,7’a-Dihydro-3’,6’-dihydroxy-spiro[naphtho[1,8-de]-1,3-dioxin-2,2’(7’H)-naphth[2,3-b]oxiren]-7’-one

Rasfarnesyltransferase inhibitor. Antifungal, antibacterial and herbicidal. Structurally unique natural products. The basic structure of palmarumycin C1 can be modified by a number of hydroxylation, oxygenation, dehydrogenation and chlorination steps. Antioxidant.

Synonyms
(1aR,7aS)-1a,7a-Dihydro-3,6-dihydroxyspiro[naphth[2,3-b]oxirene-2(7H),2’-naphtho[1,8-de][1,3]dioxin]-7-one; (1’aR,7’aS)-1’a,7’a-Dihydro-3’,6’-dihydroxy-spiro[naphtho[1,8-de]-1,3-dioxin-2,2’(7’H)-naphth[2,3-b]oxiren]-7’-one
Source
Sphaeropsidales sp.
CAS Number
159934-11-9
Molecular Formula
C₂₀H₁₂O₆
Solubility
DMSO, dichloromethane, acetone or methanol
Molecular Weight
348.3
Method for Determining Identity
Proton NMR
Purity
≥97% (HPLC)
Appearance
Yellow to green solid.
Storage and Stability
May be stored at 4°C for short-term only. Long-term storage is recommended at -20°C. Stable for 1 year after receipt. Protect from light when in solution. For maximum recovery of product, centrifuge the original vial prior to removing the cap.
Important Note
This product as supplied is intended for research use only, not for use in human, therapeutic or diagnostic applications without the expressed written authorization of United States Biological.
Toxicity and Hazards:  All products should be handled by qualified personnel only, trained in laboratory procedures.
References
1. Biologically Active Metabolites from Fungi, 4. Palmarumycins CP1-CP4 from Coniothyrium palmarum: Isolation, structure elucidation, and biological activity: K. Krohn, et al.; Liebigs Ann. Chem. 1994: 1093 (1994). 2. Biologically Active Metabolites from Fungi, 5. Palmarumycins C1-C16 from Coniothyrium sp.: Isolation, structure elucidation, and biological activity: K. Krohn, et al.; Liebigs Ann. Chem. 1994: 1099 (1994). 3. Secondary metabolites by chemical screening, 42 Cladospirones B to I from Sphaeropsidales sp. F-24'707 by variation of culture conditions: H.B. Bode, et al.; Eur. J. Org. Chem. 2000: 3185-3193 (2000). 4. Unified route to the palmarumycin and preussomerin natural products. Enantioselective synthesis of (-)- preussomerin G: A.G. Barrett, et al.; J. Org. Chem. 67: 2735-2750 (2002). 5. Natural products derived from naphthalenoid precursors by oxidative dimerization: K. Krohn; Prog. Chem. Org. Nat. Prod. 85: 1-49 (2003) (Review). 6. Antimicrobial and Antioxidant Activities and Effect of 1-Hexadecene Addition on Palmarumycin C2 and C3 Yields in Liquid Culture of Endophytic Fungus Berkleasmium sp. Dzf12: Y. Mou, et al.; Molecules 18: 15587 (2013)
USBio References
No references available
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