Difference between revisions of "Amygdalin"
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Amygdalin can be found in the seeds (kernels) of apricots<ref>Godtfredsen et al.; Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry; vol. 32; (1978); p. 588,590</ref>, bitter almonds<ref>[https://doi.org/10.1016/j.foodchem.2013.11.002 Bolarinwa, I., Orfila, C., and Morgan, M. (2014). Amygdalin content of seeds, kernels and food products commercially available in the UK. Food Chem 152(1):133-139.]</ref>, apples<ref>https://www.redalyc.org/journal/1699/169959152001/html/</ref>, peaches, cherries and plums<ref>https://www.frontiersin.org/articles/10.3389/fpls.2015.00276/full</ref>, and in the roots of manioc. | Amygdalin can be found in the seeds (kernels) of apricots<ref>Godtfredsen et al.; Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry; vol. 32; (1978); p. 588,590</ref>, bitter almonds<ref>[https://doi.org/10.1016/j.foodchem.2013.11.002 Bolarinwa, I., Orfila, C., and Morgan, M. (2014). Amygdalin content of seeds, kernels and food products commercially available in the UK. Food Chem 152(1):133-139.]</ref>, apples<ref>https://www.redalyc.org/journal/1699/169959152001/html/</ref>, peaches, cherries and plums<ref>https://www.frontiersin.org/articles/10.3389/fpls.2015.00276/full</ref>, and in the roots of manioc. | ||
| − | Amygdalin is usually extracted by finely grinding the seed kernels, then the paste is soaked in water, and the resulting mixture is either stirred or | + | Amygdalin is usually extracted by finely grinding the seed kernels, then the paste is soaked in water, and the resulting mixture is either stirred or left to shake in an [[ultrasonic cleaner|ultrasonic bath]]. A solvent extraction may be done before water is added, to remove any oils or other non-polar compounds, as amygdalin is almost insoluble in most organic solvents used for extractions, like [[chloroform]], [[dichloromethane]], [[ethyl acetate]], [[hexane]], [[toluene]]. |
An alternative way, which was how amygdalin was first discovered, is by boiling the kernels in hot ethanol. After the alcohol is removed, [[diethyl ether]] is added, which causes amygdalin to precipitate. Further recrystallization can be used to increase the purity.<ref name="Wisniak" /><ref>[https://en.wikisource.org/wiki/1911_Encyclop%C3%A6dia_Britannica/Amygdalin 1911 Encyclopædia Britannica/Amygdalin]</ref> | An alternative way, which was how amygdalin was first discovered, is by boiling the kernels in hot ethanol. After the alcohol is removed, [[diethyl ether]] is added, which causes amygdalin to precipitate. Further recrystallization can be used to increase the purity.<ref name="Wisniak" /><ref>[https://en.wikisource.org/wiki/1911_Encyclop%C3%A6dia_Britannica/Amygdalin 1911 Encyclopædia Britannica/Amygdalin]</ref> | ||
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[[Category:Aromatic compounds]] | [[Category:Aromatic compounds]] | ||
[[Category:Glycosides]] | [[Category:Glycosides]] | ||
| − | [[Category: | + | [[Category:Nitriles]] |
[[Category:Biologically-derived compounds]] | [[Category:Biologically-derived compounds]] | ||
[[Category:Materials unstable in acidic solution]] | [[Category:Materials unstable in acidic solution]] | ||
[[Category:Materials unstable in basic solution]] | [[Category:Materials unstable in basic solution]] | ||
Latest revision as of 13:11, 18 November 2023
| Names | |
|---|---|
| IUPAC name
(2R)-[β-D-Glucopyranosyl-(1→6)-β-D-glucopyranosyloxy]phenylacetonitrile
| |
| Systematic IUPAC name
(2R)-Phenyl{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile | |
| Other names
Amygdaloside
D-Mandelonitrile-β-gentiobioside D-Mandelonitrile 6-O-β-D-glucosido-β-D-glucoside | |
| Properties | |
| C20H27NO11 | |
| Molar mass | 457.429 g/mol |
| Appearance | Colorless rhombic crystals |
| Odor | Odorless (pure) Almond-like (impure) |
| Melting point | 223–226 °C (433–439 °F; 496–499 K) |
| Boiling point | Decomposes |
| 8.3 g/100 ml (10 °C)[1] | |
| Solubility | Reacts with acids, bases Poorly soluble in cold ethanol, methanol Insoluble in ethers, halocarbons, hydrocarbons |
| Solubility in chloroform | 0.029 g/100 g (15 °C)[2] |
| Solubility in ethanol | 0.14 g/100 g (10 °C) 11.4 g/100 g (78 °C) |
| Vapor pressure | ~0 mmHg |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | Non-flammable |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
522 mg/kg (rat, oral) 443 mg/kg (mice, oral) |
| Related compounds | |
| Related compounds
|
Benzaldehyde |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Amygdalin (from Ancient Greek: ἀμυγδαλή amygdalē 'almond') is a naturally occurring chemical compound found in many plants, most notably in the seeds (kernels) of apricots, bitter almonds, apples[3], peaches, cherries and plums, and in the roots of manioc.
Natural amygdalin has the (R)-configuration at the chiral phenyl center. Under mild basic conditions, this stereogenic center isomerizes; the (S)-epimer is called neoamygdalin.
Contents
Properties
Chemical
Amygdalin is classified as a cyanogenic glycoside, because each amygdalin molecule includes a nitrile group, which can be released as the toxic cyanide anion by the action of a beta-glucosidase.
Strong acids will also cleave the molecule, releasing hydrogen cyanide in air. Sulfuric acid decomposes it into d-glucose, benzaldehyde and hydrogen cyanide, while hydrochloric acid gives mandelic acid, d-glucose and ammonia.[4]
Hydrolysis of amygdalin will yield laetrile.
Physical
Amygdalin is a colorless crystalline solid, soluble in water, but mostly insoluble in organic solvents, except for hot ethanol.
Availability
Amygdalin can be found in the seeds (kernels) of apricots[5], bitter almonds[6], apples[7], peaches, cherries and plums[8], and in the roots of manioc.
Amygdalin is usually extracted by finely grinding the seed kernels, then the paste is soaked in water, and the resulting mixture is either stirred or left to shake in an ultrasonic bath. A solvent extraction may be done before water is added, to remove any oils or other non-polar compounds, as amygdalin is almost insoluble in most organic solvents used for extractions, like chloroform, dichloromethane, ethyl acetate, hexane, toluene.
An alternative way, which was how amygdalin was first discovered, is by boiling the kernels in hot ethanol. After the alcohol is removed, diethyl ether is added, which causes amygdalin to precipitate. Further recrystallization can be used to increase the purity.[4][9]
Preparation
Although amygdalin can be produced synthetically, it's quite expensive to do so, and thus it's cheaper to extract it from plants.
Projects
- Compound collecting
- Make cyanides
- Make benzaldehyde
Handling
Safety
Amygdalin is highly toxic, due to its ability to release hydrogen cyanide during its breakdown.
Amygdalin, as well as laetrile (also called "vitamin B17", even though it is not a true vitamin by any definition), its derivative, is sometimes used in alternative (aka quackery) medicine, as a "natural" treatment for cancer, however, all studies one so far show that it is completely ineffective in treating cancer as well as any other medical conditions. As a consequence of its toxicity, consuming this product is a very bad idea.
Storage
Should be kept in closed bottles.
Disposal
Can be safely neutralized with bleach and poured down the drain or in the ground.
References
- ↑ Chemist's Handbook. - T. 2. - L.-M.: Chemistry, 1964 (Справочник химика. - Т. 2. - Л.-М.: Химия, 1964)
- ↑ Solubility Handbook. - T.1, Book.2. - M.-L.: IAN USSR, 1962(Справочник по растворимости. - Т.1, Кн.2. - М.-Л.: ИАН СССР, 1962)
- ↑ https://www.sciencedirect.com/science/article/abs/pii/S0308814614013077
- ↑ 4.0 4.1 Jaime Wisniak; Pierre-Jean Robiquet; Educación Química, Volume 24, Supplement 1, March 2013, Pages 139-149
- ↑ Godtfredsen et al.; Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry; vol. 32; (1978); p. 588,590
- ↑ Bolarinwa, I., Orfila, C., and Morgan, M. (2014). Amygdalin content of seeds, kernels and food products commercially available in the UK. Food Chem 152(1):133-139.
- ↑ https://www.redalyc.org/journal/1699/169959152001/html/
- ↑ https://www.frontiersin.org/articles/10.3389/fpls.2015.00276/full
- ↑ 1911 Encyclopædia Britannica/Amygdalin
