Amygdalin Chemical Properties

Melting point:

223-226 °C

alpha 

-38.5 º (c=4, H2O)

Boiling point:

563.27°C (rough estimate)

Density 

1.4474 (rough estimate)

refractive index 

-40 ° (C=2, H2O)

storage temp. 

Sealed in dry,Room Temperature

solubility 

H₂O: 0.1 g/mL hot, clear to very faintly turbid, colorless

pka

12.69±0.70(Predicted)

form 

Powder

color 

White to Off-white

optical activity

[α]20/D 39±2°, c = 2% in H2O

Water Solubility 

83 g/L (25 ºC)

Merck 

14,597

BRN 

66856

Stability:

Hygroscopic

InChIKey

XUCIJNAGGSZNQT-SWRVSKMJSA-N

LogP

-2.237 (est)

CAS DataBase Reference

29883-15-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

26-36/37/39-45-24/25

RIDADR 

2811

WGK Germany 

3

RTECS 

OO8450000

F 

10-21

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29389090

Hazardous Substances Data

29883-15-6(Hazardous Substances Data)

Toxicity

LD50 orl-rat: 522 mg/kg WJMDA2 134,97,81

MSDS

• Language:English Provider:(R)-Laenitrile
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Amygdalin Usage And Synthesis

Uses and Synthetic Methods of Amygdalin

Amygdalin is a β-cyano-glycoside in the bitter almond that is bound to cyano (CN), which releases free cyano groups after eating the bitter almond, so that the food is poisoned. Amygdalin is a product of the metabolism of phenylalanine in the bitter almond. Amygdalin has β-glucosidase and amygdalinase (oxynitrilase): the former catalyzed amygdalin into two molecules of glucose and one molecule of amygdalenone through hydrolysis; the later catalyzes mandelonitrile into almond nitrile cyanide (HCN) and benzaldehyde through hydrolysis. Amygdalin exists in seeds, such as almonds.
Many plant root cells contain glycosides, with no toxic effect when in sugar type. Glycosides hydrolysis produce toxic substances leading to cell death. Mandelic glycosides contained in peach root is a glycoside. Amylose hydrolysis produce two kinds of plant toxins-hydrogen cyanide and benzaldehyde. Peeling root lesion formation and necrosis occurred in the vicinity of the stabbed nematode but not in contact zone; in addition, in vitro tests have proved that the pratylenchus penetrans can make amygdalin hydrolysis.
As a cyanide containing glucoside, it can be used as a substrate for such as maltase, almond casein and β-glucosidase identification, differentiation and characterization.

Category

Toxic substances

Toxicity classification

Highly toxic

Acute toxicity

Acute toxicity Oral-Rat LD50: 522 mg/kg; Oral-mouse LD50: 443 mg/kg

Flammability Hazardous properties

Combustible; producing toxic nitrogen oxides when heated.

Storage and transportation

Ventilation, low temperature, drying

Fire extinguishing agent

Dry powder, foam, sand, carbon dioxide

Description

Amygdalin is a cyanogenic glycoside that has been found in seeds from plants of the Rosaceae family and has diverse biological activities. It induces cell cycle arrest at the G₀/G₁ phase, decreases cyclin A and Cdk2 levels, and inhibits cell growth in UMUC-3, RT112, and TCCSUP bladder cancer cells when used at concentrations ranging from 1.25 to 10 mg/ml. Amygdalin (3 mg/kg) reduces the number of primary microtubules and microvessels in aortic rings isolated from rats with diabetes induced by streptozotocin . In vivo, amygdalin reduces triglyceride, total cholesterol, and LDL levels and aortic sinus plaque area in an LDLR^-/- mouse model of atherosclerosis. It also reduces production of TNF-α, IL-1β, and IL-6, as well as neutrophil and macrophage infiltration, in bronchoalveolar lavage fluid (BALF) in a mouse model of LPS-induced acute lung injury.

Chemical Properties

WHITE FINE CRYSTALLINE POWDER

Uses

antiinflammatory, experimental antineoplastic

Uses

Amygdalin, a cyanide containing glycoside, may be used as a substrate to identify, differentiate and characterize enzymes such as maltase(s), emulsin(s) and β-glucosidase(s).

Uses

A cyanogenic glycoside occurring in seeds of Rosaceae, principally in bitter almonds and peach and apricot pits. Some time ago it was said to be effective in the treatment of cancer, but controlled clinical trials repeatedly failed to confirm such claims.

Definition

ChEBI: An amygdalin in which the stereocentre on the cyanohydrin function has R-configuration.

World Health Organization (WHO)

Laetrile, which consists mainly of amydgalin, a glycoside extracted from the kernels of apricots, peaches and other fruits, has been available for over 30 years in preparations purporting to be beneficial in the treatment of cancer. Although there is no evidence that these are efficacious, preparations continued to be widely used and, until the late 1970s, they were considered to be harmless. However, oral dosage forms, which may be broken down in the gut to hydrogen cyanide, have subsequently been shown to be potentially lethal. This has resulted in restrictive regulatory measures in several countries.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biochem/physiol Actions

Cyanogenic glycoside that is a component of bitter almonds and apricot pits. There is no scientific evidence that amygdalin itself is an effective anti-cancer agent. Recent studies using β?glucoside linked to a tumor-associated monoclonal antibody to release cyanide at the tumor cell has shown significant cytotoxicity.

Safety Profile

Human poison by ingestion(infant data). Poison experimentally by ingestion. Anexperimental teratogen. Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx.

Purification Methods

D-Amygdalin recrystallises from water as the trihydrate, or from EtOH. It is present in bitter almonds. [Smith Chem Ber 64 1115 1931, Beilstein 17/8 V 188.]

Amygdalin(29883-15-6)Related Product Information

• CYCLANDELATE
• DL-Mandelic acid
• Phenylhydrazine
• Mandelic acid
• PHENYL VALERATE
• VITAMIN K1
• DGL
• Bitter Apricot Seed Extract
• Vitamin B6
• Mandelonitrile
• AMAROGENTIN
• Benzeneacetonitrile
• amygdalin90+%
• Amygdalin
• D(-)-AMYGDALIN MONOHYDRATE
• amygdalin beta(1-6)glucosidase
• Amygdalin(Vb17)
• AMYGDALIN-ISO-HYDROCHLORIDE