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Glycosides and other natural products

Amygdalin

Also known as (R)-Amygdalin, D-Amygdalin, (R)-Laenitrile

CAS 29883-15-6Formula C20H27NO11Molar mass 457.43 g/molEC 249-925-3
GHS signal word: Warning. Pictograms: Harmful or irritant 43 suppliers listed
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Amygdalin chemical structure, C20H27NO11, CAS 29883-15-6
2D chemical structure

Key facts

What buyers check first

All properties
CAS number
29883-15-6
Formula
C20H27NO11
Melting point
223 to 226
Solubility
VERY SOL IN HOT WATER, SLIGHTLY SOL IN ALCOHOL, INSOL IN ETHER, CHLOROFORM, SOL IN HOT A…
HS code
293890
Category
Glycosides and other natural products

What is Amygdalin?

Plain description, key identifiers and synonyms

(R)-amygdalin is an amygdalin in which the stereocentre on the cyanohydrin function has R-configuration. It has a role as an antineoplastic agent, an apoptosis inducer and a plant metabolite. It is functionally related to a (R)-mandelonitrile.

Amygdalin is a cyanogenic glycoside present in kernels of fruit.

Identifiers

Registry numbers, names and line notations, tap to copy

IUPAC name
(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
CAS number
29883-15-6 CAS number cross-checked
EC number
249-925-3
Molecular formula
C20H27NO11
UNII
214UUQ9N0H
MDL number
MFCD00006598, MFCD00866428
InChIKey
XUCIJNAGGSZNQT-JHSLDZJXSA-N
InChI
InChI=1S/C20H27NO11/c21-6-10(9-4-2-1-3-5-9)30-20-18(28)16(26)14(24)12(32-20)8-29-19-17(27)15(25)13(23)11(7-22)31-19/h1-5,10-20,22-28H,7-8H2/t10-,11+,12+,13+,14+,15-,16-,17+,18+,19+,20+/m0/s1
Canonical SMILES
N#CC(OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O)c1ccccc1
Isomeric SMILES
C1=CC=C(C=C1)[C@H](C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)O

Synonyms

  • (R)-Amygdalin
  • D-Amygdalin
  • (R)-Laenitrile
  • (R)-Amygdaloside
  • R-Amygdalin
  • D(-)-Mandelonitrile-beta-D-gentiobioside
  • D-Mandelonitrile-beta-D-glucosido-6-beta-D-glucoside
  • Glucoprunasin
  • (-)-D-mandelonitrile beta-D-gentiobioside
  • (2R)-[(6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy](phenyl)acetonitrile
  • (R)-alpha-((6-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl)oxy)benzeneacetonitrile
  • Benzeneacetonitrile, alpha-((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)-, (R)-
  • (2R)-((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)(phenyl)acetonitrile
  • Mandelonitrile beta Gentiobioside
  • (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
  • 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)oxy)methyl)oxan-2-yl)oxy)acetonitrile
  • ((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)(phenyl)acetonitrile
  • Benzeneacetonitrile,a-[(6-O-b-D-glucopyranosyl-b-D-glucopyranosyl)oxy]-, (aR)-
  • 5-17-08-00118 (Beilstein Handbook Reference)
  • D-Mandelonitrile-beta-gentiobioside
  • (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]oxy}methyl)oxan-2-yl]oxy}acetonitrile
  • D-(-)-mandelonitrile-beta-D-gentiobioside
  • (R)-alpha-((6-O-beta-D-glucopyranosyl-beta-D-
  • (R)-alpha-((6-O-beta-D-glucopyranosyl-beta-D- glucopyranosyl)oxy)benzeneacetonitrile
  • (r)-alpha-((6-o-beta-d-glucopyranosyl-beta-d-glucopyranosyl)oxy)benzeneaceto
Show all 26 synonyms
  • Benzeneacetonitrile, alpha-[(6-O-beta-D-glucopyransoyl-beta-D-glucopyranosyl)oxy]-, (R)-

Physical and chemical properties

Measured values and descriptors computed from the structure

Physical and chemical properties

Measured values, check the supplier specification for your grade

Melting point
223 to 226exp.
Solubility
VERY SOL IN HOT WATER, SLIGHTLY SOL IN ALCOHOL, INSOL IN ETHER, CHLOROFORM, SOL IN HOT ALCOHOLexp.

Values vary by grade. Ask suppliers for the COA or TDS of the batch you buy.

Computed descriptors

Calculated from the structure, useful for screening and formulation

Molecular weight
457.43 g/molcalc.
Exact mass
457.1584 Dacalc.
LogP (octanol/water)
-3.11calc.
Topological polar surface area
202.3 Ųcalc.
Hydrogen bond donors
7calc.
Hydrogen bond acceptors
12calc.
Rotatable bonds
7calc.
Heavy atoms
32calc.
Rings
3calc.
Aromatic rings
1calc.
Fraction sp3 carbons
0.65calc.
Formal charge
0calc.
Stereocentres
11calc.
Lipinski rule of five
Fails (2 violations)calc.

Calculated for screening. Confirm critical figures with the supplier.

Murcko scaffold

The ring system that remains when every side chain is removed

Murcko scaffold of this chemical, c1ccc(COC2CCCC(COC3CCCCO3)O2)cc1

c1ccc(COC2CCCC(COC3CCCCO3)O2)cc1

3 rings, 22 atoms.

32 other chemicals share this scaffold

Safety and hazards

GHS classification summary, not a safety data sheet

GHS signal word
Warning
GHS07: Harmful or irritant
Harmful or irritant

Hazard statements

  • H302Harmful if swallowed.
Precautionary statements (5)
  • P264Wash skin thoroughly after handling.
  • P270Do not eat, drink or smoke when using this product.
  • P301 + P317If swallowed: Get medical help.
  • P330Rinse mouth.
  • P501Dispose of contents and container in accordance with local regulations.

GHS classification summary, not a safety data sheet (SDS). Classifications can differ by supplier, grade and concentration. Always check the supplier's SDS.

Full safety data and first aid

Amygdalin suppliers

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Where suppliers are based

43 suppliers in 6 countries

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Amygdalin price

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Uses and applications

What the substance is used for, by industry and function

Pharmacological actions

  • Antineoplastic Agents, Phytogenic

Roles

  • antineoplastic agent
  • apoptosis inducer
  • eukaryotic metabolite
  • metabolite
  • pharmaceutical
  • plant metabolite

Pharmacology

Amygdalin is a cyanogenic glucoside isolated from almonds and seeds of other plants of the family Rosaceae. Amygdalin is converted by plant emulsin (a combination of a glucosidase and a nitrilase) or hydrochloric acid into benzaldehyde, D-glucose, and hydrocyanic acid. (NCI04)

How it is made

Occurs in seeds of rosaceae, principally in bitter almonds, also in peaches & apricots. Obtained by extracting defatted almond meal repeatedly with boiling 95% alcohol.

Regulatory status

Inventories, regulations and trade controls that list this substance

No regulatory list memberships are recorded for this substance yet. Always check the rules of the importing and exporting country before trade.

HS code and trade data

Customs classification and reported world trade statistics

Global trade

World import and export statistics for the HS code Amygdalin is traded under.

HS 2938.90Indicative HS code

Natural or reproduced by synthesis, other than rutoside (rutin) and its derivatives

World exports in 2024
$1.4B
−8.3% vs 2023, imports $1.35B
2019 to 2024
Top exporters
  1. China49.2%
  2. France * partner reported8.9%
  3. Malaysia6.1%
Top importers
  1. United States22.3%
  2. India * partner reported7.8%
  3. Brazil5.5%

* Partner reported figures, a lower bound.

Reported customs values in USD, not prices.Full trade data

The HS code shown for Amygdalin is indicative (it was assigned by structure rules). Confirm the classification with your customs broker before shipping.

Frequently asked questions

Quick answers about Amygdalin, based on the data on this page

What is Amygdalin?

(R)-amygdalin is an amygdalin in which the stereocentre on the cyanohydrin function has R-configuration. It has a role as an antineoplastic agent, an apoptosis inducer and a plant metabolite. It is functionally related to a (R)-mandelonitrile.

Is Amygdalin hazardous?

Amygdalin carries the GHS signal word "Warning". Main hazards: harmful if swallowed. This summary is not an SDS, always read the supplier safety data sheet.

Guides for buyers

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Data last updated 7 Oct 2026. Details may have changed, please confirm them with the supplier. Report an error on this page
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