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MedKoo Cat#: 585208 | Name: Sylvaticin

Description:

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

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

Chemical Structure

Sylvaticin
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: 638.93

Elemental Analysis: C, 69.56; H, 10.41; O, 20.03

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
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 638.93 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: 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.

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