Sambunigrin

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

MedKoo CAT#: 597899

CAS#: 99-19-4

Description: Sambunigrin is a cyanogenic glycoside.


Chemical Structure

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Sambunigrin
CAS# 99-19-4

Theoretical Analysis

MedKoo Cat#: 597899
Name: Sambunigrin
CAS#: 99-19-4
Chemical Formula: C14H17NO6
Exact Mass: 295.1056
Molecular Weight: 295.29
Elemental Analysis: C, 56.95; H, 5.80; N, 4.74; O, 32.51

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: Sambunigrin; (S)-Prunasin; (2S)-Sambunigrin; L-Prunasin;

IUPAC/Chemical Name: (S)-2-phenyl-2-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)acetonitrile

InChi Key: ZKSZEJFBGODIJW-YOVYLDAJSA-N

InChi Code: InChI=1S/C14H17NO6/c15-6-9(8-4-2-1-3-5-8)20-14-13(19)12(18)11(17)10(7-16)21-14/h1-5,9-14,16-19H,7H2/t9-,10-,11-,12+,13-,14-/m1/s1

SMILES Code: N#C[C@@H](O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C2=CC=CC=C2

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 295.29 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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8: Song MC, Yang HJ, Jeong TS, Kim KT, Baek NI. Heterocyclic compounds from Chrysanthemum coronarium L. and their inhibitory activity on hACAT-1, hACAT-2, and LDL-oxidation. Arch Pharm Res. 2008 May;31(5):573-8. doi: 10.1007/s12272-001-1195-4. Epub 2008 May 15. PubMed PMID: 18481011.

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11: Miller RE, Stewart M, Capon RJ, Woodrow IE. A galloylated cyanogenic glycoside from the Australian endemic rainforest tree Elaeocarpus sericopetalus (Elaeocarpaceae). Phytochemistry. 2006 Jul;67(13):1365-71. Epub 2006 May 22. PubMed PMID: 16716370.

12: Christensen J, Jaroszewski JW. Natural glycosides containing allopyranose from the passion fruit plant and circular dichroism of benzaldehyde cyanohydrin glycosides. Org Lett. 2001 Jul 12;3(14):2193-5. PubMed PMID: 11440577.

13: Hösel W, Tober I, Eklund SH, Conn EE. Characterization of beta-glucosidases with high specificity for the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) moench seedlings. Arch Biochem Biophys. 1987 Jan;252(1):152-62. PubMed PMID: 3101594.

14: Petruccioli M, Brimer L, Cicalini AR, Pulci V, Federici F. Production and properties of the linamarase and amygdalase activities of Penicillium aurantiogriseum P35. Biosci Biotechnol Biochem. 1999 May;63(5):805-12. PubMed PMID: 10380623.

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16: Senica M, Stampar F, Veberic R, Mikulic-Petkovsek M. The higher the better? Differences in phenolics and cyanogenic glycosides in Sambucus nigra leaves, flowers and berries from different altitudes. J Sci Food Agric. 2017 Jun;97(8):2623-2632. doi: 10.1002/jsfa.8085. Epub 2016 Nov 10. PubMed PMID: 27734518.