Amygdalin

Amygdalin Basic information
Uses and Synthetic Methods of Amygdalin Category Toxicity classification Acute toxicity Flammability Hazardous properties Storage and transportation Fire extinguishing agent
Product Name:Amygdalin
Synonyms:(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;Amygdalin 29883-15-6
CAS:29883-15-6
MF:C20H27NO11
MW:457.43
EINECS:249-925-3
Product Categories:Miscellaneous Natural Products;Biochemistry;Disaccharides;Glycosides;Sugars;Natural Plant Extract;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;natural product;Inhibitors;organic acids;Nutritional Ingredients;Herb extract
Mol File:29883-15-6.mol
Amygdalin Structure
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
form Powder
pka12.69±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
InChIKeyXUCIJNAGGSZNQT-SWRVSKMJSA-N
LogP-2.237 (est)
CAS DataBase Reference29883-15-6(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
10-21
HazardClass 6.1(b)
PackingGroup III
HS Code 29389090
Hazardous Substances Data29883-15-6(Hazardous Substances Data)
ToxicityLD50 orl-rat: 522 mg/kg WJMDA2 134,97,81
MSDS Information
ProviderLanguage
(R)-Laenitrile English
SigmaAldrich English
ALFA English
Amygdalin Usage And Synthesis
Uses and Synthetic Methods of AmygdalinAmygdalin 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.

CategoryToxic substances
Toxicity classificationHighly toxic
Acute toxicityAcute toxicity Oral-Rat LD50: 522 mg/kg; Oral-mouse LD50: 443 mg/kg
Flammability Hazardous propertiesCombustible; producing toxic nitrogen oxides when heated.
Storage and transportationVentilation, low temperature, drying
Fire extinguishing agentDry powder, foam, sand, carbon dioxide
DescriptionAmygdalin 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 PropertiesWHITE FINE CRYSTALLINE POWDER
Usesantiinflammatory, experimental antineoplastic
UsesAmygdalin, 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).
UsesA 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.
DefinitionChEBI: 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 DescriptionThis 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 ActionsCyanogenic 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 ProfileHuman poison by ingestion(infant data). Poison experimentally by ingestion. Anexperimental teratogen. Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx.
Purification MethodsD-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 Preparation Products And Raw materials
Preparation ProductsBenzaldehyde-->Bitter almond oil-->(R)-(+)-ALPHA-HYDROXYBENZENE-ACETONITRILE
VITAMIN K1 Bitter Apricot Seed Extract DGL AMYGDALIN TRIHYDRATE AMAROGENTIN amygdalin beta(1-6)glucosidase DL-Mandelic acid Amygdalin(Vb17) PHENYL-[3,4,5-TRIHYDROXY-6-(3,4,5-TRIHYDROXY-6-HYDROXYMETHYL-TETRAHYDRO-PYRAN-2-YLOXYMETHYL)-TETRAHYDRO-PYRAN-2-YLOXY]-ACETONITRILE Benzeneacetonitrile PHENYL VALERATE AMYGDALIN-ISO-HYDROCHLORIDE D(-)-AMYGDALIN MONOHYDRATE Mandelonitrile Amygdalin CYCLANDELATE Phenylhydrazine Mandelic acid

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