Sambucinol

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

MedKoo CAT#: 461744

CAS#: 90044-33-0

Description: Sambucinol is a trichothecene analog.


Chemical Structure

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Sambucinol
CAS# 90044-33-0

Theoretical Analysis

MedKoo Cat#: 461744
Name: Sambucinol
CAS#: 90044-33-0
Chemical Formula: C15H22O4
Exact Mass: 266.1518
Molecular Weight: 266.33
Elemental Analysis: C, 67.65; H, 8.33; O, 24.03

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.

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Synonym: Sambucinol;

IUPAC/Chemical Name: (2S,3R,3aR,4aR,8aR,8bR)-3a-(hydroxymethyl)-6,8a,8b-trimethyl-1,2,3,3a,7,8,8a,8b-octahydro-3,4a-epoxycyclopenta[b]benzofuran-2-ol

InChi Key: GFLMBFRNOPTZDK-CMBQYIQPSA-N

InChi Code: InChI=1S/C15H22O4/c1-9-4-5-12(2)13(3)7-10(17)11-14(13,8-16)19-15(12,6-9)18-11/h6,10-11,16-17H,4-5,7-8H2,1-3H3/t10-,11+,12+,13+,14+,15+/m0/s1

SMILES Code: C[C@@]12C[C@H](O)[C@H]([C@]23CO)O[C@@]4(O3)C=C(C)CC[C@]14C

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: 2934.99.03.00

Preparing Stock Solutions

The following data is based on the product molecular weight 266.33 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

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1: Zamir LO, Nikolakakis A, Huang L, St-Pierre P, Sauriol F, Sparace S, Mamer O. Biosynthesis of 3-acetyldeoxynivalenol and sambucinol. Identification of the two oxygenation steps after trichodiene. J Biol Chem. 1999 Apr 30;274(18):12269-77. PubMed PMID: 10212195.

2: Zamir LO, Devor KA, Nikolakakis A, Sauriol F. Biosynthesis of Fusarium culmorum trichothecenes. The roles of isotrichodermin and 12,13-epoxytrichothec-9-ene. J Biol Chem. 1990 Apr 25;265(12):6713-25. Erratum in: J Biol Chem 1990 Sep 5;265(25):15347. PubMed PMID: 2182627.

3: Wang Y, Zhang L, Li GT, Li ZH, Dong ZJ, Li Y, Liu JK. Identification and Cytotoxic Activities of Two New Trichothecenes and a New Cuparane-Type Sesquiterpenoid from the Cultures of the Mushroom Engleromyces goetzii. Nat Prod Bioprospect. 2015 Jan 30. [Epub ahead of print] PubMed PMID: 25633363; PubMed Central PMCID: PMC4328002.

4: Zamir LO, Nikolakakis A, Sauriol F, Mamer O. Biosynthesis of trichothecenes and apotrichothecenes. J Agric Food Chem. 1999 May;47(5):1823-35. PubMed PMID: 10552458.

5: Zamir LO, Devor KA, Nadeau Y, Sauriol F. Structure determination and biosynthesis of a novel metabolite of Fusarium culmorum, apotrichodiol. J Biol Chem. 1987 Nov 15;262(32):15354-8. PubMed PMID: 3680200.

6: Humer E, Lucke A, Harder H, Metzler-Zebeli BU, Böhm J, Zebeli Q. Effects of Citric and Lactic Acid on the Reduction of Deoxynivalenol and Its Derivatives in Feeds. Toxins (Basel). 2016 Sep 28;8(10). pii: E285. PubMed PMID: 27690101; PubMed Central PMCID: PMC5086645.

7: Schmidt R, Zajkowski P, Wink J. Toxicity of Fusarium sambucinum Fuckel sensu lato to brine shrimp. Mycopathologia. 1995;129(3):173-5. PubMed PMID: 7566054.

8: Zamir LO, Devor KA. Kinetic pulse-labeling study of Fusarium culmorum. Biosynthetic intermediates and dead-end metabolites. J Biol Chem. 1987 Nov 15;262(32):15348-53. PubMed PMID: 3680199.

9: Young JC, Games DE. Supercritical fluid chromatography of Fusarium mycotoxins. J Chromatogr. 1992 Dec 25;627(1-2):247-54. PubMed PMID: 1487527.

10: Langseth W, Ghebremeskel M, Kosiak B, Kolsaker P, Miller D. Production of culmorin compounds and other secondary metabolites by Fusarium culmorum and F. graminearum strains isolated from Norwegian cereals. Mycopathologia. 2001;152(1):23-34. PubMed PMID: 11694092.

11: Trapp SC, Hohn TM, McCormick S, Jarvis BB. Characterization of the gene cluster for biosynthesis of macrocyclic trichothecenes in Myrothecium roridum. Mol Gen Genet. 1998 Feb;257(4):421-32. PubMed PMID: 9529523.

12: Piñeiro MS, Scott PM, Kanhere SR. Mycotoxin producing potential of Fusarium graminearum isolates from Uruguayan barley. Mycopathologia. 1995-1996;132(3):167-72. PubMed PMID: 8684431.

13: Bondy GS, McCormick SP, Beremand MN, Pestka JJ. Murine lymphocyte proliferation impaired by substituted neosolaniols and calonectrins--Fusarium metabolites associated with trichothecene biosynthesis. Toxicon. 1991;29(9):1107-13. PubMed PMID: 1796475.