Sylvaticin

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

MedKoo CAT#: 585208

CAS#: 129312-45-4

Description: Sylvaticin is a cytotoxic and insecticidal acetogenin from Rollinia sylvatica (Annonaceae).


Chemical Structure

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Sylvaticin
CAS# 129312-45-4

Theoretical Analysis

MedKoo Cat#: 585208
Name: Sylvaticin
CAS#: 129312-45-4
Chemical Formula: C37H66O8
Exact Mass: 638.4758
Molecular Weight: 638.927
Elemental Analysis: C, 69.56; H, 10.41; O, 20.03

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: Sylvaticin

IUPAC/Chemical Name: (2S)-4-[(2R)-9-[(5S)-5-[(4S)-1,4-dihydroxy-4-[(2R,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]butyl]oxolan-2-yl]-2-hydroxynonyl]-2-methyl-2H-furan-5-one

InChi Key: HKMBLJVHVBJAIH-NZPKVYSJSA-N

InChi Code: InChI=1S/C37H66O8/c1-3-4-5-6-7-8-12-15-18-31(39)35-23-24-36(45-35)33(41)21-20-32(40)34-22-19-30(44-34)17-14-11-9-10-13-16-29(38)26-28-25-27(2)43-37(28)42/h25,27,29-36,38-41H,3-24,26H2,1-2H3/t27-,29+,30?,31-,32?,33-,34-,35+,36+/m0/s1

SMILES Code: O=C1C(C[C@H](O)CCCCCCCC2O[C@H](C(O)CC[C@H](O)[C@@H]3O[C@@H]([C@@H](O)CCCCCCCCCC)CC3)CC2)=C[C@H](C)O1

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

Preparing Stock Solutions

The following data is based on the product molecular weight 638.927 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: Lascombe MB, Retailleau P, Ponchet M, Industri B, Blein JP, Prangé T. Structure of sylvaticin, a new alpha-elicitin-like protein from Pythium sylvaticum. Acta Crystallogr D Biol Crystallogr. 2007 Oct;63(Pt 10):1102-8. Epub 2007 Sep 19. PubMed PMID: 17881828.

2: Donohoe TJ, Harris RM, Williams O, Hargaden GC, Burrows J, Parker J. Concise syntheses of the natural products (+)-sylvaticin and (+)-cis-sylvaticin. J Am Chem Soc. 2009 Sep 9;131(35):12854-61. doi: 10.1021/ja9049959. PubMed PMID: 19673528.

3: Mikolajczak KJ, Madrigal RV, Rupprecht JK, Hui YH, Liu YM, Smith DL, McLaughlin JL. Sylvaticin: a new cytotoxic and insecticidal acetogenin from Rollinia sylvatica (Annonaceae). Experientia. 1990 Mar 15;46(3):324-7. Review. PubMed PMID: 2178957.

4: Lascombe MB, Ponchet M, Cardin L, Milat ML, Blein JP, Prangé T. Purification, crystallization and preliminary X-ray studies of sylvaticin, an elicitin-like protein from Pythium sylvaticum. Acta Crystallogr D Biol Crystallogr. 2004 Feb;60(Pt 2):362-4. Epub 2004 Jan 23. PubMed PMID: 14747726.

5: Brown LJ, Spurr IB, Kemp SC, Camp NP, Gibson KR, Brown RC. Total synthesis of cis-sylvaticin. Org Lett. 2008 Jun 19;10(12):2489-92. doi: 10.1021/ol800767e. Epub 2008 May 20. PubMed PMID: 18489103.

6: Shimada H, Kozlowski JF, Mclaughlin JL. The localisations in liposomal membranes of the tetrahydrofuran ring moieties of the annonaceous acetogenins, annonacin and sylvaticin, as determined by 1H NMR spectroscopy. Pharmacol Res. 1998 May;37(5):357-64. PubMed PMID: 9642031.

7: Bhunnoo RA, Hobbs H, Lainé DI, Light ME, Brown RC. Synthesis of the non-adjacent bis-THF core of cis-sylvaticin using a double oxidative cyclisation. Org Biomol Chem. 2009 Mar 7;7(5):1017-24. doi: 10.1039/b813201a. Epub 2009 Jan 28. PubMed PMID: 19225685.

8: Donohoe TJ, Harris RM, Burrows J, Parker J. Total synthesis of (+)-cis-sylvaticin: double oxidative cyclization reactions catalyzed by osmium. J Am Chem Soc. 2006 Oct 25;128(42):13704-5. PubMed PMID: 17044695.

9: Spurr IB, Brown RC. Total synthesis of annonaceous acetogenins belonging to the non-adjacent bis-THF and non-adjacent THF-THP sub-classes. Molecules. 2010 Jan 21;15(1):460-501. doi: 10.3390/molecules15010460. PubMed PMID: 20110904; PubMed Central PMCID: PMC6257053.

10: Alali FQ, Kaakeh W, Bennett GW, McLaughlin JL. Annonaceous acetogenins as natural pesticides: potent toxicity against insecticide-susceptible and -resistant German cockroaches (Dictyoptera: Blattellidae). J Econ Entomol. 1998 Jun;91(3):641-9. PubMed PMID: 9650513.

11: Tolosa D, Alvarez CO, Bardón A, Neske A. Insecticidal effects of acetogenins from Rollinia occidentalis seed extract. Nat Prod Commun. 2012 Dec;7(12):1645-6. PubMed PMID: 23413573.

12: Février A, Ferreira ME, Fournet A, Yaluff G, Inchausti A, Rojas de Arias A, Hocquemiller R, Waechter AI. Acetogenins and other compounds from Rollinia emarginata and their antiprotozoal activities. Planta Med. 1999 Feb;65(1):47-9. PubMed PMID: 10083845.