Oudemansin

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

MedKoo CAT#: 584907

CAS#: 73341-71-6

Description: Oudemansin has strong antifungal properties and inhibits respiration in fungi.

Chemical Structure

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Oudemansin
CAS# 73341-71-6
Instruction

Theoretical Analysis

MedKoo Cat#: 584907
Name: Oudemansin
CAS#: 73341-71-6
Chemical Formula: C17H22O4
Exact Mass: 290.15
Molecular Weight: 290.359
Elemental Analysis: C, 70.32; H, 7.64; O, 22.04

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Oudemansin

IUPAC/Chemical Name: 5-Hexenoic acid, 4-methoxy-2-(methoxymethylene)-3-methyl-6-phenyl-, methyl ester, (S-(R*,R*-(E,E)))-

InChi Key: COBDENJOXQSLKO-NKAAJRRHSA-N

InChi Code: InChI=1S/C17H22O4/c1-13(15(12-19-2)17(18)21-4)16(20-3)11-10-14-8-6-5-7-9-14/h5-13,16H,1-4H3/b11-10+,15-12+/t13-,16-/m0/s1

SMILES Code: O=C(OC)/C([C@H](C)[C@@H](OC)/C=C/C1=CC=CC=C1)=C/OC

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: 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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 290.36 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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Reconstitution Calculator

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1: Anke T, Besl H, Mocek U, Steglich W. Antibiotics from basidiomycetes. XVIII. Strobilurin C and oudemansin B, two new antifungal metabolites from Xerula species (Agaricales). J Antibiot (Tokyo). 1983 Jun;36(6):661-6. PubMed PMID: 6874589.

2: Becker WF, von Jagow G, Anke T, Steglich W. Oudemansin, strobilurin A, strobilurin B and myxothiazol: new inhibitors of the bc1 segment of the respiratory chain with an E-beta-methoxyacrylate system as common structural element. FEBS Lett. 1981 Sep 28;132(2):329-33. PubMed PMID: 6271595.

3: Anke T, Werle A, Bross M, Steglich W. Antibiotics from basidiomycetes. XXXIII. Oudemansin X, a new antifungal E-beta-methoxyacrylate from Oudemansiella radicata (Relhan ex Fr.) Sing. J Antibiot (Tokyo). 1990 Aug;43(8):1010-1. PubMed PMID: 2211348.

4: Akita H. [Natural products syntheses based on the biotransformation using biocatalyst]. Yakugaku Zasshi. 2011 Feb;131(2):269-84. Review. Japanese. PubMed PMID: 21297373.

5: Anke T, Hecht HJ, Schramm G, Steglich W. Antibiotics from basidiomycetes. IX. Oudemansin, an antifungal antibiotic from Oudemansiella mucida (Schrader ex Fr.) Hoehnel (Agaricales). J Antibiot (Tokyo). 1979 Nov;32(11):1112-7. PubMed PMID: 528381.

6: Engler M, Anke T, Sterner O. Production of antibiotics by Collybia nivalis, Omphalotus olearis, a Favolaschia and a Pterula species on natural substrates. Z Naturforsch C. 1998 May-Jun;53(5-6):318-24. PubMed PMID: 9705612.

7: Brandt U, Schägger H, von Jagow G. Characterisation of binding of the methoxyacrylate inhibitors to mitochondrial cytochrome c reductase. Eur J Biochem. 1988 May 2;173(3):499-506. PubMed PMID: 3371345.

8: Wood KA, Kau DA, Wrigley SK, Beneyto R, Renno DV, Ainsworth AM, Penn J, Hill D, Killacky J, Depledge P. Novel beta-methoxyacrylates of the 9-methoxystrobilurin and oudesmansin classes produced by the basidiomycete Favolaschia pustulosa. J Nat Prod. 1996 Jul;59(7):646-9. PubMed PMID: 8926488.

9: Uchiro H, Nagasawa K, Kotake T, Hasegawa D, Tomita A, Kobayashi S. The first synthesis and antifungal activities of 9-methoxystrobilurin-type beta-substituted beta-methoxyacrylate. Bioorg Med Chem Lett. 2002 Oct 21;12(20):2821-4. PubMed PMID: 12270154.

10: Brandt U, Haase U, Schägger H, von Jagow G. Significance of the "Rieske" iron-sulfur protein for formation and function of the ubiquinol-oxidation pocket of mitochondrial cytochrome c reductase (bc1 complex). J Biol Chem. 1991 Oct 25;266(30):19958-64. PubMed PMID: 1657909.

11: Clough JM. The strobilurins, oudemansins, and myxothiazols, fungicidal derivatives of beta-methoxyacrylic acid. Nat Prod Rep. 1993 Dec;10(6):565-74. Review. PubMed PMID: 8121648.

12: Engler-Lohr M, Anke T, Hellwig V, Steglich W. Noroudemansin A, a new antifungal antibiotic from Pterula species 82168 and three semisynthetic derivatives. Z Naturforsch C. 1999 Mar-Apr;54(3-4):163-8. Erratum in: Z Naturforsch [C] 1999 Jul-Aug;54(7-8):617. PubMed PMID: 10349735.

13: Sasse F, Böhlendorf B, Herrmann M, Kunze B, Forche E, Steinmetz H, Höfle G, Reichenbach H. Melithiazols, new beta-methoxyacrylate inhibitors of the respiratory chain isolated from myxobacteria. Production, isolation, physico-chemical and biological properties. J Antibiot (Tokyo). 1999 Aug;52(8):721-9. Erratum in: J Antibiot (Tokyo) 2000 Jun;53(6):C-4. Hermann M [corrected to Herrmann M]. PubMed PMID: 10580385.