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Linamarin

Linamarin structure

Linamarin 

structure
  • CAS No:

    554-35-8

  • Formula:

    C10H17NO6

  • Chemical Name:

    Linamarin

  • Synonyms:

    Propanenitrile,2-(β-D-glucopyranosyloxy)-2-methyl-;Linamarin;2-(β-D-Glucopyranosyloxy)-2-methylpropanenitrile;α-Hydroxyisobutyronitrile β-D-glucose;Phaseolunatin;2-(β-D-Glucosyloxy)-2-methylpropionitrile;30372-72-6;1194765-62-2

Description

White Crystalline Solid


Solid


Linamarin is a beta-D-glucoside. It derives from a 2-hydroxy-2-methylpropanenitrile.

Linamarin Basic Attributes

247.247

247.25

H3V9RP3WLO

DTXSID8052857

NEEDLES

29400090

Characteristics

123

-1.8

Solid

1.41g/cm3

142-143 °C

473.3ºC at 760mmHg

240ºC

1.549

FREELY SOL IN WATER, COLD ALCOHOL, HOT ACETONE; SLIGHTLY SOL IN HOT ETHYL ACETATE, ETHER, BENZENE, CHLOROFORM; PRACTICALLY INSOL IN PETROLEUM ETHER

SPECIFIC OPTICAL ROTATION: -29 DEG @ 18 °C/D

BITTER

157.3 Ų [M+Na]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

NONH for all modes of transport

3

20/22-36/37/38

26-36

TZ4850000

Xn

Acid Sensitive

P261-P305 + P351 + P338

H302-H315-H319-H332-H335

EVOLVES HYDROGEN CYANIDE WITH LINSEED MEAL BUT NOT WITH EMULSIN

A REVIEW CONCERNING THE ROLE OF LINAMARIN IN CASSAVA TOXICITY.[BOURDOUX P ET AL; CASSAVA TOXICITY: THE ROLE OF LINAMARIN; INT DEV RES CENT (TECH REP) IDRC: IDRC-136E, ROLE CASSAVA ETIOL ENDEM GOITRE CRETINISM 15, 167 (1980)]

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

RATS WERE FED A SEMIPURIFIED DIET PROVIDING 10% CASEIN SUPPLEMENTED WITH METHIONINE FOR 2 WEEKS, AT WHICH TIME SOME ANIMALS RECEIVED THE SAME DIET WITHOUT THE METHIONINE FOR 4 DAYS. ANIMALS THAT RECEIVED LINAMARIN WERE GIVEN A SINGLE ORAL DOSE CONTAINING 500 OR 250 MG/KG BODY WEIGHT. AT THE LOWER LINAMARIN DOSE DIETARY SUPPLEMENTATION WITH METHIONINE APPEARED TO REDUCE INCIDENCES OF CLINICAL TOXICITY SIGNS AND FATALITIES. DIETARY SUPPLEMENTATION WITH METHIONINE PROVIDED SOME PROTECTION AGAINST THE TOXICITY OF THE LOWER LEVEL OF LINAMARIN ADMINISTERED.

FROM THE SEED SKINS OR EMBRYOS OF FLAX...|/GLYCOSIDE IN/ CASSAVA, A TROPICAL PLANT...|THE ISOLATION AND IDENTIFICATION OF LINAMARIN FROM PASSIFLORA WARMINGII IS REPORTED.

Drug Information

WISTAR RATS, ABOUT 100 G IN WEIGHT, WERE DOSED BY STOMACH TUBE WITH 30 MG OF PURE LINAMARIN (A MAJOR CYANOGENIC GLUCOSIDE IN CASSAVA). NO INTACT LINAMARIN WAS IDENTIFIED IN THE FECES OR BLOOD BUT 5.65 MG WAS EXCRETED IN THE URINE ALONG WITH 0.823 MG OF THIOCYANATE ION.|THE AMNIOTIC FLUIDS AND BLOOD SAMPLES OF 40 PREGNANT WOMEN WERE ANALYZED FOR THIOCYANATE. THE CONCENTRATION IN THE AMNIOTIC FLUIDS VARIED FROM 0.66-3.88 MMOL/L WHILE THOSE OF THE BLOOD SAMPLES VARIED FROM 0.70-2.80 MMOL/L. THE HIGHEST CONCENTRATIONS OCCURRED IN THE LOWER CLASS WHO EAT A LOT OF GARI (CASSAVA PUDDING), WHICH IS THE STAPLE DIET THAT CONTAINS THE CYANOGENIC GLYCOSIDE LINAMARIN. THE DETOXIFICATION PRODUCT, THIOCYANATE, SEEMS TO PENETRATE THE PLACENTAL BARRIER. THE IMPLICATION OF THIS IN THE ETIOLOGY OF GOITER AND CRETINISM WAS DISCUSSED.

THE BIOSYNTHESIS OF LINAMARIN FROM RADIOACTIVE VALINE OR ACETONE CYANOHYDRIN BY UDP-GLUCOSE-DEPENDENT KETONE CYANOHYDRIN GLUCOSYLTRANSFERASE IN FLAX SEEDLINGS WAS INHIBITED BY PREINCUBATION OF FLAX SEEDLINGS WITH ISOLEUCINE, THE PRECURSOR OF LOTAUSTRALIN.

FOLLOWING INGESTION BY RATS OF LINAMARIN-CONTAINING CASSAVA, THE EXPERIMENTAL OBSERVATIONS OF CHANGES IN IODINE AND THIOCYANATE METABOLISM CORRELATE WITH THE METABOLIC FINDINGS REPORTED FOR SUBJECTS LIVING IN THE GOITROUS AREA OF THE IDJWI ISLAND. THE ENDEMIC GOITER PREVAILING THERE IS APPARENTLY RELATED TO THE SIMULTANEOUS EFFECT OF IODINE DEFICIENCY AND CONSUMPTION OF LARGE AMOUNTS OF CASSAVA.

1-cyano-1-methylethyl beta-D-glucoside

Linamarin Use and Manufacturing

Uses

Can be found in the seed skins and embryos of flax

THE USE OF CASSAVA POSES A NUMBER OF PROBLEMS. CASSAVA CONTAINS LINAMARIN, WHICH ON HYDROLYSIS YIELDS HYDROCYANIC ACID, WHICH IS TOXIC TO ANIMALS. IN SMALL DOSES, CYANIDE IS DETOXIFIED TO THIOCYANATE BY THE ENZYME RHODANASE, MAKING USE OF METHIONINE AS THE SULFUR DONOR. THIS AMINO ACID BECOMES THE FIRST LIMITING FACTOR IN CASSAVA FEEDS. WITH PROPER MANAGEMENT CASSAVA CAN BE USED AS A SUBSTITUTE FOR MAIZE IN ANIMAL FEED.

A NEW PAPER CHROMATOGRAPHY METHOD FOR DETERMINATION OF INTACT CYANOGENIC GLUCOSIDE LINAMARIN.|THIN-LAYER CHROMATOGRAPHIC QUANTIFICATION OF CYANOGENIC COMPOUNDS.

Computed Properties

Molecular Weight:247.24
XLogP3:-1.8
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:3
Exact Mass:247.10558726
Monoisotopic Mass:247.10558726
Topological Polar Surface Area:123
Heavy Atom Count:17
Complexity:311
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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