(alphaS)-alpha-(beta-D-glucopyranosyloxy)-4-hydroxybenzeneacetonitrile

Synopsis, Chemistry

ANALYTICAL SOLUTION(s)

2 Other Ref. Standards

2 Other Ref. Standards

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(alphaS)-alpha-(beta-D-glucopyranosyloxy)-4-hydroxybenzeneacetonitrile

Also known as: 499-20-7, (s)-(beta-d-glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile, (s)-4-hydroxymandelonitrile beta-d-glucoside, P5999iy65c, (2s)-2-(4-hydroxyphenyl)-2-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile, C14h17no7

Molecular Formula

C₁₄H₁₇NO₇

Molecular Weight

311.29 g/mol

InChI Key

NVLTYOJHPBMILU-YOVYLDAJSA-N

FDA UNII

P5999IY65C

dhurrin is a natural product found in Campylospermum flavum, Ostrya virginiana, and other organisms with data available.

1 2D Structure

(alphaS)-alpha-(beta-D-glucopyranosyloxy)-4-hydroxybenzeneacetonitrile

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-(4-hydroxyphenyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile

2.1.2 InChI

InChI=1S/C14H17NO7/c15-5-9(7-1-3-8(17)4-2-7)21-14-13(20)12(19)11(18)10(6-16)22-14/h1-4,9-14,16-20H,6H2/t9-,10-,11-,12+,13-,14-/m1/s1

2.1.3 InChI Key

NVLTYOJHPBMILU-YOVYLDAJSA-N

2.1.4 Canonical SMILES

C1=CC(=CC=C1C(C#N)OC2C(C(C(C(O2)CO)O)O)O)O

2.1.5 Isomeric SMILES

C1=CC(=CC=C1[C@@H](C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O

2.2 Other Identifiers

2.2.1 UNII

P5999IY65C

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 499-20-7

2. (s)-(beta-d-glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile

3. (s)-4-hydroxymandelonitrile Beta-d-glucoside

4. P5999iy65c

5. (2s)-2-(4-hydroxyphenyl)-2-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile

6. C14h17no7

7. (2s)-(beta-d-glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile

8. (alphas)-alpha-(beta-d-glucopyranosyloxy)-4-hydroxybenzeneacetonitrile

9. Unii-p5999iy65c

10. Einecs 207-878-6

11. Dhurrin [mi]

12. Schembl50174

13. Dhurrin, >=95% (hplc)

14. Chebi:27826

15. Dtxsid90198142

16. 1e55

17. Zinc4096638

18. Mfcd18632527

19. (s)-4-hydroxymandelonitrile-beta-d-glucoside

20. C05143

21. P-hydroxy-s-mandelonitrile-beta-d-glucopyranoside

22. (s)-p-hydroxymandelnitrile-beta-d-glucopyranoside

23. Q908811

24. Beta-d-glucopyranosyloxy-(s)-p-hydroxymandelonitrile

25. .beta.-d-glucopyranosyloxy-l-p-hydroxymandelonitrile

26. Benzeneacetonitrile, Alpha-(beta-d-glucopyranosyloxy)-4-hydroxy-, (alphas)-

27. (.alpha.s)-.alpha.-(.beta.-d-glucopyranosyloxy)-4-hydroxybenzeneacetonitrile

28. (2s)-2-(4-hydroxyphenyl)-2-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]acetonitrile

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₁₄H₁₇NO₇
Molecular Weight	311.29 g/mol
XLogP3	-0.9
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	4
Exact Mass	311.10050188 g/mol
Monoisotopic Mass	311.10050188 g/mol
Topological Polar Surface Area	143 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	403
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1