Amygdalin

Modify Date: 2024-01-01 19:01:02

Amygdalin structure	Common Name	Amygdalin
	CAS Number	29883-15-6	Molecular Weight	457.428
	Density	1.6±0.1 g/cm3	Boiling Point	743.3±60.0 °C at 760 mmHg
	Molecular Formula	C₂₀H₂₇NO₁₁	Melting Point	223-226 °C(lit.)
	MSDS	Chinese USA	Flash Point	403.3±32.9 °C
	Symbol	GHS07	Signal Word	Warning

Use of Amygdalin

Amygdalin is a plant glucoside isolated from the stones of rosaceous fruits, such as apricots, peaches, almond, cherries, and plums.

Name	Amygdalin
Synonym	More Synonyms

Description	Amygdalin is a plant glucoside isolated from the stones of rosaceous fruits, such as apricots, peaches, almond, cherries, and plums.
Related Catalog	Signaling Pathways >> Others >> Others Research Areas >> Cancer Natural Products >> Saccharides and Glycosides
In Vitro	Amygdalin has antitumor activity. Some advances had been made on the antitumor mechanism of amygdalin[1]. Amygdalin downregulates especially genes belonging to cell cycle category: exonuclease 1, ATP-binding cassette, sub-family F, member 2, MRE11 meiotic recombination 11 homolog A, topoisomerase (DNA) I, and FK506 binding protein 12-rapamycin-associated protein 1. RT-PCR analysis reveals that mRNA levels of these genes are also decreased by amygdalin treatment in SNU-C4 human colon cancer cells[2].
In Vivo	Amygdalin is effective at alleviating inflammatory pain and that it can be used as an analgesic with anti-nociceptive and anti-inflammatory activities. The intramuscular injection of amygdalin significantly reduced the formalin-induced tonic pain in both early (the initial 10 min after formalin injection) and late phases (10-30 min following the initial formalin injection). During the late phase, amygdalin reduces the formalin-induced pain in a dose-dependentmanner in a dose range less than 1 mg/kg[3].
Cell Assay	Cell viability is determined by MTT assay. Cells are seeded in triplicate at a concentration of 1×105 cells/well on a 96-well plate. SNU-C4 cells are treated with amygdalin at concentrations of 0.25, 0.5, 2.5, and 5 mg/mL for 24 h. After MTT is added to each group, the cells are incubated for 4 h. Then, they are further incubated for 1 h, including the solution in which MTT is dissolved[2].
Animal Admin	Rats: The amygdalin powder is dissolved in saline and diluted with appropriate medium. Male Sprague–Dawley rats weighing 230-250 g are used for this experiment. 50mL of 5% formalin are injected to produce fomalin-induced pain in the rats. Thirty minutes before the formalin injection to induce pain, the rats are given an intramuscular injection of amygdalin solution (0.1, 0.5, 1.0, 10 mg/kg), or saline as a vehicle control[3].
References	[1]. Song Z, et al. Advanced research on anti-tumor effects of amygdalin. J Cancer Res Ther. 2014 Aug;10 Suppl 1:3-7. [2]. Park HJ,et al. Amygdalin inhibits genes related to cell cycle in SNU-C4 human colon cancer cells. World J Gastroenterol. 2005 Sep 7;11(33):5156-61. [3]. Hwang HJ,et al. Antinociceptive effect of amygdalin isolated from Prunus armeniaca on formalin-induced pain in rats. Biol Pharm Bull. 2008 Aug;31(8):1559-64.

Density	1.6±0.1 g/cm3
Boiling Point	743.3±60.0 °C at 760 mmHg
Melting Point	223-226 °C(lit.)
Molecular Formula	C₂₀H₂₇NO₁₁
Molecular Weight	457.428
Flash Point	403.3±32.9 °C
Exact Mass	457.158417
PSA	202.32000
LogP	-0.36
Vapour Pressure	0.0±2.6 mmHg at 25°C
Index of Refraction	1.650
Water Solubility	83 g/L (25 ºC)

Amygdalin MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OO8450000

CHEMICAL NAME :: D(-)-Mandelonitrile-beta-D-gentiobioside

CAS REGISTRY NUMBER :: 29883-15-6

BEILSTEIN REFERENCE NO. :: 0066856

LAST UPDATED :: 199612

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C20-H27-N-O11

MOLECULAR WEIGHT :: 457.48

WISWESSER LINE NOTATION :: T6OTJ BOYR&CN CQ DQ EQ F1O- BT6OTJ CQ DQ EQ F1Q -D(-)

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - infant

DOSE/DURATION :: 50 mg/kg

TOXIC EFFECTS :: Behavioral - coma Lungs, Thorax, or Respiration - dyspnea Gastrointestinal - nausea or vomiting

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 405 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 443 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory stimulation

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 167 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 6 gm/kg/30D-I

TOXIC EFFECTS :: Blood - pigmented or nucleated red blood cells Blood - changes in erythrocyte (RBC) count Blood - changes in leukocyte (WBC) count

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 300 mg/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - musculoskeletal system

MUTATION DATA

TYPE OF TEST :: Host-mediated assay

TEST SYSTEM :: Rodent - mouse Bacteria - Salmonella typhimurium

DOSE/DURATION :: 250 mg/kg

REFERENCE :: SCIEAS Science. (American Assoc. for the Advancement of Science, 1333 H St., NW, Washington, DC 20005) V.1- 1895- Volume(issue)/page/year: 198,625,1977 *** REVIEWS *** TOXICOLOGY REVIEW CTOXAO Clinical Toxicology. (New York, NY) V.1-18, 1968-81. For publisher information, see JTCTDW. Volume(issue)/page/year: 17,85,1980 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5264 No. of Facilities: 427 (estimated) No. of Industries: 1 No. of Occupations: 5 No. of Employees: 3566 (estimated) No. of Female Employees: 2900 (estimated)

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H302
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Faceshields;Gloves
Hazard Codes	Xn:Harmful
Risk Phrases	R22
Safety Phrases	S26-S36/37/39-S45
RIDADR	2811
WGK Germany	3
RTECS	OO8450000
Packaging Group	III
Hazard Class	6.1(b)

Precursor 0
DownStream 7
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Optimization of technological procedure for amygdalin isolation from plum seeds (Pruni domesticae semen).

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Mandelonitrile b-Glucuronide

Vitamin B17

rile

(2R)-{[6-O-(β-D-Glucopyranosyl)-β-D-glucopyranosyl]oxy}(phenyl)acetonitrile

Mygdalin

D-amygdalin

EINECS 249-925-3

(2R)-Phenyl{[(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

Mandelonitrile-b-gentiobioside

amygdaloside

D-Mandelonitrile 6-O-β-D-glucosido-β-D-glucoside

(2R)-{[6-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl]oxy}(phenyl)ethanenitrile

D-AMYGLADIN

D-Mandelonitrile-β-gentiobioside

Laetrile

Nitrilosides

mandelonitrile-β-gentiobioside

(R)-amygdalin

D-Mandelonitrile-b-D-glucosido-6-b-D-glucoside

Benzeneacetonitrile, α-[(6-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-, (αR)-

[(6-O-b-D-Glucopyranosyl-b-D-glucopyranosyl)oxy]benzeneacetonitrile

Amygdalin

MFCD00006598

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Amygdalin

Use of Amygdalin

Names

Amygdalin Biological Activity

Chemical & Physical Properties

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

Safety Information

Precursor & DownStream

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