Amygdalin

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

Amygdalin Structure
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
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.

 Names

Name Amygdalin
Synonym More Synonyms

 Amygdalin Biological Activity

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

 Chemical & Physical Properties

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)

 Toxicological Information

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)

 Safety Information

Symbol GHS07
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)

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 Synonyms

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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