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

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 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 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

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.


Dilution Calculator

Calculate the dilution required to prepare a stock solution.

1: Buhrmester RA, Ebinger1a JE, Seigler DS. Sambunigrin and cyanogenic variability in populations of Sambucus canadensis L. (Caprifoliaceae). Biochem Syst Ecol. 2000 Aug 1;28(7):689-695. PubMed PMID: 10854744.

2: Møller BL, Olsen CE, Motawia MS. General and Stereocontrolled Approach to the Chemical Synthesis of Naturally Occurring Cyanogenic Glucosides. J Nat Prod. 2016 Apr 22;79(4):1198-202. doi: 10.1021/acs.jnatprod.5b01121. Epub 2016 Mar 9. PubMed PMID: 26959700.

3: Franks TK, Hayasaka Y, Choimes S, van Heeswijck R. Cyanogenic glucosides in grapevine: polymorphism, identification and developmental patterns. Phytochemistry. 2005 Jan;66(2):165-73. PubMed PMID: 15652573.

4: Bourjot M, Leyssen P, Eydoux C, Guillemot JC, Canard B, Rasoanaivo P, Guéritte F, Litaudon M. Chemical constituents of Anacolosa pervilleana and their antiviral activities. Fitoterapia. 2012 Sep;83(6):1076-80. doi: 10.1016/j.fitote.2012.05.004. Epub 2012 May 14. PubMed PMID: 22613073.

5: Campa C, Schmitt-Kopplin P, Cataldi TR, Bufo SA, Freitag D, Kettrup A. Analysis of cyanogenic glycosides by micellar capillary electrophoresis. J Chromatogr B Biomed Sci Appl. 2000 Feb 28;739(1):95-100. PubMed PMID: 10744317.

6: Le NH, Malterud KE, Diallo D, Paulsen BS, Nergård CS, Wangensteen H. Bioactive polyphenols in Ximenia americana and the traditional use among Malian healers. J Ethnopharmacol. 2012 Feb 15;139(3):858-62. doi: 10.1016/j.jep.2011.12.031. Epub 2011 Dec 27. PubMed PMID: 22212502.

7: Saeki D, Yamada T, Kajimoto T, Muraoka O, Tanaka R. A set of two diastereomers of cyanogenic glycosides from Passiflora quadrangularis. Nat Prod Commun. 2011 Aug;6(8):1091-4. PubMed PMID: 21922906.

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.

9: Egli KL. Screening test for amygdalin in tablets, solutions, powders, and seeds. J Assoc Off Anal Chem. 1979 Mar;62(2):308-9. PubMed PMID: 447603.

10: Seigler DS, Pauli GF, Nahrstedt A, Leen R. Cyanogenic allosides and glucosides from Passiflora edulis and Carica papaya. Phytochemistry. 2002 Aug;60(8):873-82. PubMed PMID: 12150815.

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.

15: Thygesen LG, Jørgensen K, Møller BL, Engelsen SB. Raman spectroscopic analysis of cyanogenic glucosides in plants: development of a flow injection surface-enhanced Raman scatter (FI-SERS) method for determination of cyanide. Appl Spectrosc. 2004 Feb;58(2):212-7. PubMed PMID: 15000716.

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.