ChemicalBook CAS DataBase List 29883-15-6

29883-15-6

Name	Amygdalin
CAS	29883-15-6
EINECS(EC#)	249-925-3
Molecular Formula	C20H27NO11
MDL Number	MFCD00006598
Molecular Weight	457.43
MOL File	29883-15-6.mol

Synonyms

6-O-BETA-D-GLUCOSIDO-BETA-D-GLUCOSIDE AMYGDALIN BENZENEACETONITRILE-[(6-O-BETA-D-GLUCOPYRANOSYL-BETA-D-GLUCOPYRANOSYL)OXY]-, (R)- D(-)-AMYGDALIN D-AMYGDALIN D-AMYGDALIN HYDRATE D-MANDELONITRILE 6-O-BETA-D-GLUCOSIDO-BETA-D-GLUCOSIDE D-MANDELONITRILE 6-O-BETA-D-GLUCOSIDO-BETA-D-GLUCOSIDE D-MANDELONITRILE BETA-GENTIOBIOSIDE D-MANDELONITRILE-BETA-D-GLUCOSIDO-6-BETA-D-GLUCOSIDE D-MANDELONITRILE-BETA-GENTIOBIOSIDE GLUCOPRUNASIN LAETRILE MANDELONITRILE GENTIOBIOSIDE (r)-alpha-((6-o-beta-d-glucopyranosyl-beta-d-glucopyranosyl)oxy)benzeneaceto (r)-alpha-((6-o-beta-d-glucopyranosyl-beta-d-glucopyranosyl)oxy)benzeneacetonit (r)-oxy) (r)-y) amygdaloside benzeneacetonitrile,alpha-((6-o-beta-d-glucopyranosyl-beta-d-glucopyranosyl) benzeneacetonitrile,alpha-((6-o-beta-d-glucopyranosyl-beta-d-glucopyranosyl)ox

Chemical Properties

Appearance	WHITE FINE CRYSTALLINE POWDER
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
form	Powder
pka	12.69±0.70(Predicted)
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 Data

Hazard Codes	Xn
Risk Statements	R22:Harmful if swallowed. less more
Safety Statements	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 label where possible) . less more
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 less more

Raw materials And Preparation Products

Hazard Information

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 (Item No. 13104). 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

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.]

Material Safety Data Sheet(MSDS)

Questions And Answer

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;

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29883-15-6

Chemical Properties

Safety Data

Raw materials And Preparation Products

Preparation Products

Hazard Information

Description

Chemical Properties

Uses

Definition

World Health Organization (WHO)

General Description

Biochem/physiol Actions

Safety Profile

Purification Methods

Material Safety Data Sheet(MSDS)

Questions And Answer

Uses and Synthetic Methods of Amygdalin

Category

Toxicity classification

Acute toxicity

Flammability Hazardous properties

Storage and transportation

Fire extinguishing agent

Spectrum Detail

Well-known Reagent Company Product Information

Supplier

Related Products