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MedKoo Cat#: 414924 | Name: Phenoxan

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Phenoxan is isolated from Polyangium; inhibits electron transport at NADH-ubiquinone oxidoreductase.

Chemical Structure

Phenoxan
Phenoxan
CAS#134332-63-1

Theoretical Analysis

MedKoo Cat#: 414924

Name: Phenoxan

CAS#: 134332-63-1

Chemical Formula: C23H25NO4

Exact Mass: 379.1784

Molecular Weight: 379.46

Elemental Analysis: C, 72.80; H, 6.64; N, 3.69; O, 16.87

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Phenoxan; NSC 650914; NSC650914; NSC-650914
IUPAC/Chemical Name
4H-Pyran-4-one, 3-ethyl-6-methoxy-5-methyl-2-(2-((3E)-3-methyl-4-phenyl-3-butenyl)-4-oxazolyl)-
InChi Key
OFVMLCJEDYAOIB-FYWRMAATSA-N
InChi Code
InChI=1S/C23H25NO4/c1-5-18-21(25)16(3)23(26-4)28-22(18)19-14-27-20(24-19)12-11-15(2)13-17-9-7-6-8-10-17/h6-10,13-14H,5,11-12H2,1-4H3/b15-13+
SMILES Code
O=C1C(CC)=C(C2=COC(CC/C(C)=C/C3=CC=CC=C3)=N2)OC(OC)=C1C
Appearance
Solid powder
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 379.46 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.

Recalculate based on batch purity %
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: Kunze B, Jansen R, Pridzun L, Jurkiewicz E, Hunsmann G, Höfle G, Reichenbach H. Phenoxan, a new oxazole-pyrone from myxobacteria: production, antimicrobial activity and its inhibition of the electron transport in complex I of the respiratory chain. J Antibiot (Tokyo). 1992 Sep;45(9):1549-52. doi: 10.7164/antibiotics.45.1549. PMID: 1429243. 2: Garey D, Ramirez Ml ML, Gonzales S, Wertsching A, Tith S, Keefe K, Peña MR. An Approach to Substituted 4-Hydroxypyran-2-ones: The Total Synthesis of Phenoxan. J Org Chem. 1996 Jul 12;61(14):4853-4856. doi: 10.1021/jo960221g. PMID: 11667430. 3: Uslu R, Bonavida B. Involvement of the mitochondrion respiratory chain in the synergy achieved by treatment of human ovarian carcinoma cell lines with both tumor necrosis factor-alpha and cis-diamminedichloroplatinum. Cancer. 1996 Feb 15;77(4):725-32. PMID: 8616765. 4: Friedrich T, van Heek P, Leif H, Ohnishi T, Forche E, Kunze B, Jansen R, Trowitzsch-Kienast W, Höfle G, Reichenbach H, et al. Two binding sites of inhibitors in NADH: ubiquinone oxidoreductase (complex I). Relationship of one site with the ubiquinone-binding site of bacterial glucose:ubiquinone oxidoreductase. Eur J Biochem. 1994 Jan 15;219(1-2):691-8. doi: 10.1111/j.1432-1033.1994.tb19985.x. PMID: 8307034. 5: Rozhdestvensky LM, Mikhailov VF, Schlyakova TG, Shagirova JM, Shchegoleva RA, Raeva NF, Lisina NI, Shulenina LV, Zorin VV, Pchelka AV, Trubitsina KY. [Searching Radiation Countermeasures using the Model of Prolonged Irradiation of Mice with Low Dose Rate and Evaluation of Their Influence on Heat Shock Protein Genes Expression]. Radiats Biol Radioecol. 2015 Jul-Aug;55(4):420-30. Russian. PMID: 26601542. 6: Serebrianyĭ AM, Zoz NN. Stimulirovannaia repopuliatsiia kak osnova fenomenov antimutageneza i adaptivnogo otveta u rasteniĭ [Stimulated repopulation as a basis of antimutagenesis and the adaptive response in plants]. Genetika. 2002 Mar;38(3):340-6. Russian. PMID: 11963562. 7: Kanazawa S, Mizuno S, Yamauchi R, Nishimura N, Maeba I. Synthesis of 5-hydroxy-2-(beta-D-ribofuranosyl)pyran-4-one from a pyranulose glycoside. Carbohydr Res. 1999 May 31;318(1-4):180-5. doi: 10.1016/s0008-6215(99)00098-1. PMID: 10515056. 8: Serebrianyĭ AM, Zoz NN. Radiatsionnyĭ adaptivnyĭ otvet u pshenitsy. Fenomenologiia i veroiatnyĭ mekhanizm [Radiation adaptive response in wheat. Phenomenology and possible mechanism]. Radiats Biol Radioecol. 2001 Sep- Oct;41(5):589-98. Russian. PMID: 11721352. 9: Shishkina LN, Poliakova NV, Mazaletskaia LI, Bespal'ko OF, Kushnireva EV. Protivoluchevye svoĭstva fenoksana pri nizkointensivnom gamma-obluchenii v maloĭ doze [Radioprotective properties of phenoxane during low intensity low dose gamma irradiation]. Radiats Biol Radioecol. 1999 Mar-Jun;39(2-3):322-8. Russian. PMID: 10366964.