Uses and Synthetic Methods of Amygdalin Category Toxicity classification Acute toxicity Flammability Hazardous properties Storage and transportation Fire extinguishing agent
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Amygdalin

Uses and Synthetic Methods of Amygdalin Category Toxicity classification Acute toxicity Flammability Hazardous properties Storage and transportation Fire extinguishing agent
Product Name
Amygdalin
CAS No.
29883-15-6
Chemical Name
Amygdalin
Synonyms
D-AMYGDALIN;vitamin b17;Bitter AlMond extract;D(-)-AMYGDALIN;LAETRILE;D,L-AMYGDALIN;D-AMYGDALIN HYDRATE;(r)-alpha-((6-o-beta-d-glucopyranosyl-beta-d-glucopyranosyl)oxy)benzeneaceto;(r)-alpha-((6-o-beta-d-glucopyranosyl-beta-d-glucopyranosyl)oxy)benzeneacetonit;rile
CBNumber
CB8363552
Molecular Formula
C20H27NO11
Formula Weight
457.43
MOL File
29883-15-6.mol
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Amygdalin Property

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)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
10050
Product name
Amygdalin
Purity
BioXtra, ≥97.0% (HPLC)
Packaging
5g
Price
$105
Updated
2024/03/01
Sigma-Aldrich
Product number
10050
Product name
Amygdalin
Purity
BioXtra, ≥97.0% (HPLC)
Packaging
25g
Price
$419
Updated
2024/03/01
TCI Chemical
Product number
A0443
Product name
Amygdalin
Purity
>97.0%(HPLC)
Packaging
1g
Price
$28
Updated
2024/03/01
Alfa Aesar
Product number
J61472
Product name
D-Amygdalin, 98%
Packaging
1g
Price
$30.65
Updated
2024/03/01
Alfa Aesar
Product number
J61472
Product name
D-Amygdalin, 98%
Packaging
5g
Price
$77.65
Updated
2024/03/01
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Amygdalin Chemical Properties,Usage,Production

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 Preparation Products And Raw materials

Raw materials

Preparation Products

Bitter almond oil Benzaldehyde
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View Lastest Price from Amygdalin manufacturers

HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
Amygdalin 29883-15-6
Price
US $980.00-750.00/ton
Min. Order
1ton
Purity
99%
Supply Ability
5000
Release date
2024-08-15
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Vitamin B17 / Amygdalin 29883-15-6
Price
US $180.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-04-23
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Amygdalin 29883-15-6
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
98%min HPLC
Supply Ability
500kgs
Release date
2021-08-11

29883-15-6, AmygdalinRelated Search:

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

  • (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
  • 2-(hydroxymethyl)-6-[[3,4,5-trihydroxy-6-(methoxymethyl)-2-oxanyl]methoxymethyl]oxane-3,4,5-triol
  • D(-)-Amygdalin hydrate,95%
  • [(6-O-Hexopyranosylhexopyranosyl)-oxy](phenyl)-acetonitrile
  • AMYGDALIN
  • 6-O-BETA-D-GLUCOSIDO-BETA-D-GLUCOSIDE
  • d(-)-mandelonitrile-beta-d-gentiobioside
  • mandelonitrile-beta-gentiobioside
  • nsc-15780
  • rile
  • 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
  • Amygdalin,D-Mandelonitrile 6-O-β-D-glucosido-β-D-glucoside, D-Mandelonitrile-β-gentiobioside, Laetrile
  • D-Amygdalin, 98+%
  • D-Amygdalin,D-Mandelonitrile β-gentiobioside, D-Mandelonitrile 6-O-β-D-glucosido-β-D-glucoside, D-Mandelonitrile-β-gentiobioside, Amygdalin, Laetrile
  • D-Mandelonitrile-β-gentiobioside ,98%
  • Benzeneacetonitrile,alpha-((6-o-beta-d-glucopyranosyl-beta-d-glucopyr
  • AMygdalin(VitaMin B17
  • AMygdaloside (disaccharide)
  • Nitrilosides
  • (R)-2-phenyl-2-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxyMethyl)tetrahydro-2H-pyran-2-yl)oxy)Methyl)tetrahydro-2H-pyran-2-yl)oxy)acetonitrile
  • AMygdalin /VB17/Laetrile
  • AMygdalin /VB17/Laetril
  • Bitter AlMond extract
  • D-Mandelonitrile 6-O-β-D-glucosido-β-D-glucoside
  • D-Mandelonitrile-β-gentiobioside
  • Mygdalin
  • D-AMYGDALIN FROM APRICOT KERNELS
  • AMYGDALIN: BENZENEACETONITRILE,-[(6-O--D-GLUCOPYRANOSYL--D-GLUCOPYRANOSYL)OXY]-, (R)-
  • D-Amygdalin (1.12428)
  • D-Amygdalinhydrate,96%
  • Benzeneacetonitrile, .alpha.-(6-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy-, (.alpha.R)-
  • d-mandelonitrile-á-d-glucosido-6-á-d-glucoside
  • vitamin b17
  • D-Mandelonitrile-b-gentiobioside
  • AMYGDALIN(RG)
  • D,L-AMYGDALIN
  • (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
  • (R)-Amygdalin
  • (R)-Amygdaloside
  • (R)-Laenitrile
  • AMYGDALIN BIOXTRA, >= 97.0% (HPLC)