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29883-15-6

Basic Information
CAS No.: 29883-15-6
Name: Amygdalin
Article Data: 4
Cas Database
Molecular Structure:
Molecular Structure of 29883-15-6 (Amygdalin)
Formula: C20H27NO11
Molecular Weight: 457.434
Synonyms: Amygdalin(6CI,7CI,8CI);Benzeneacetonitrile, a-[(6-O-b-D-glucopyranosyl-b-D-glucopyranosyl)oxy]-, (R)-;(-)-Amygdalin;(R)-Amygdalin;Amygdaloside;Amygdaloside (disaccharide);D-Amygdalin;Mandelonitrile-b-gentiobioside;
EINECS: 249-925-3
Density: 1.59 g/cm3
Melting Point: 223-226 °C(lit.)
Boiling Point: 743.3 °C at 760 mmHg
Flash Point: 403.3 °C
Solubility: 83 g/L (25 °C) in water
Appearance: white fine crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: 26-36/37/39-45
Transport Information: UN 2811
PSA: 202.32000
LogP: -3.10802
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Chemistry

Molecular Structure of Amygdalin (CAS NO.29883-15-6):

IUPAC Name: (2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile 
Empirical Formula: C20H27NO11
Molecular Weight: 457.4285
H bond acceptors: 12
H bond donors: 7
Freely Rotating Bonds: 14
Polar Surface Area: 125.32 Å2
Index of Refraction: 1.649
Molar Refractivity: 104.9 cm3
Molar Volume: 287.6 cm3
Surface Tension: 92.9 dyne/cm
Density: 1.59 g/cm3
Flash Point: 403.3 °C
Enthalpy of Vaporization: 113.75 kJ/mol
Boiling Point: 743.3 °C at 760 mmHg
Vapour Pressure: 3.35E-23 mmHg at 25°C
Melting point: 223-226 °C(lit.)
Water Solubility 83 g/L (25 ºC)
Merck 14,597
BRN 66856
EINECS: 249-925-3
Product Categories: Miscellaneous Natural Products; Biochemistry; Disaccharides; Glycosides; Sugars; Natural Plant Extract
InChI
InChI=1/C20H27NO11/c21-6-10(9-4-2-1-3-5-9)30-20-18(28)16(26)14(24)12(32-20)8-29-19-17(27)15(25)13(23)11(7-22)31-19/h1-5,10-20,22-28H,7-8H2/t10?,11-,12-,13-,14-,15+,16+,17-,18-,19-,20-/m1/s1
Smiles
O1[C@@H](O[C@@H](c2ccccc2)C#N)[C@@H]([C@@H](O)[C@@H]([C@H]1CO[C@@H]1O[C@@H]([C@@H](O)[C@@H]([C@H]1O)O)CO)O)O

History

  Amygdalin (CAS NO.29883-15-6) is a glycoside initially isolated from the seeds of the tree Prunus dulcis, also known as bitter almonds, by Pierre-Jean Robiquet and A. F. Boutron-Charlard in 1803, and subsequently investigated by Liebig and Wohler in 1830, and others. Several other related species in the genus of Prunus, including apricot (Prunus armeniaca) and black cherry (Prunus serotina), also contain amygdalin. It was promoted as a cancer cure by Ernst T. Krebs under the name "Vitamin B17", but studies have found it to be ineffective.

Uses

  Amygdalin (CAS NO.29883-15-6) was first isolated in 1830. In 1845 it was used for cancer in Russia and again in the 1920s in the United States, but it was considered too poisonous. In the 1950s a reportedly nontoxic, synthetic form was patented for use as a meat preservative and later marketed as Laetrile for cancer treatment.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo oral 100mg/kg (100mg/kg)   National Technical Information Service. Vol. PB288-559,
infant LDLo oral 50mg/kg (50mg/kg) BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: NAUSEA OR VOMITING
JAMA, Journal of the American Medical Association. Vol. 238, Pg. 482, 1977.
monkey LDLo oral 167mg/kg (167mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
National Technical Information Service. Vol. PB288-559,
mouse LD50 oral 443mg/kg (443mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 29, Pg. 1291, 1987.
rat LD50 oral 405mg/kg (405mg/kg)   National Technical Information Service. Vol. PB288-558,

Safety Profile

Human poison by ingestion (infant data). Poison experimentally by ingestion. An experimental teratogen. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: HarmfulXn
Risk Statements: 22 
R22:Harmful if swallowed.
Safety Statements: 26-36/37/39-45 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: 2811
WGK Germany: 3
RTECS: OO8450000
F: 10-21
HazardClass: 6.1(b)
PackingGroup: III

Specification

  Amygdalin , with CAS number of 29883-15-6, can be called Benzeneacetonitrile, a-[(6-O-b-D-glucopyranosyl-b-D-glucopyranosyl)oxy]-, (R)- ; (-)-Amygdalin ; Mandelonitrile-b-gentiobioside ; Amygdaloside (disaccharide) ; (R)-Amygdalin . It is a white fine crystalline powder.