dhurrin (Q908811)

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chemical compound
  • (alphaS)-alpha-(beta-D-glucopyranosyloxy)-4-hydroxybenzeneacetonitrile
  • (S)-(beta-D-glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile
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Language Label Description Also known as
English
dhurrin
chemical compound
  • (alphaS)-alpha-(beta-D-glucopyranosyloxy)-4-hydroxybenzeneacetonitrile
  • (S)-(beta-D-glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile

Statements

chemical structure
Dhurrin.png
671 × 474; 9 KB
0 references
mass
311.100502 dalton
1 reference
stated in
PubChem
PubChem CID
161355
language of work or name
English
title
Dhurrin (English)
retrieved
5 October 2016
chemical formula
C₁₄H₁₇NO₇
1 reference
stated in
PubChem
PubChem CID
161355
language of work or name
English
title
Dhurrin (English)
retrieved
20 November 2016
canonical SMILES
C1=CC(=CC=C1C(C#N)OC2C(C(C(C(O2)CO)O)O)O)O
1 reference
stated in
PubChem
PubChem CID
161355
language of work or name
English
title
Dhurrin (English)
retrieved
20 November 2016
isomeric SMILES
C1=CC(=CC=C1[C@@H](C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O
1 reference
stated in
PubChem
PubChem CID
161355
language of work or name
English
title
Dhurrin (English)
retrieved
20 November 2016
found in taxon
Sorghum bicolor
11 references
stated in
Dhurrin-6'-glucoside, a cyanogenic diglucoside from Sorghum bicolor
stated in
Dhurrin synthesis in sorghum is regulated at the transcriptional level and induced by nitrogen fertilization in older plants
stated in
Tissue Distributions of Dhurrin and of Enzymes Involved in Its Metabolism in Leaves of Sorghum bicolor
stated in
Leakage of Dhurrin and p-Hydroxybenzaldehyde from Young Sorghum Shoots Immersed in Various Solvents
stated in
Biosynthesis of the Cyanogenic Glucoside Dhurrin in Seedlings of Sorghum bicolor (L.) Moench and Partial Purification of the Enzyme System Involved
stated in
Turnover of dhurrin in green sorghum seedlings
stated in
The primary sequence of cytochrome P450tyr, the multifunctional N-hydroxylase catalyzing the conversion of L-tyrosine to p-hydroxyphenylacetaldehyde oxime in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench
stated in
2-nitro-3-(p-hydroxyphenyl)propionate and aci-1-nitro-2-(p-hydroxyphenyl)ethane, two intermediates in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench.
stated in
Cytochrome P-450TYR is a multifunctional heme-thiolate enzyme catalyzing the conversion of L-tyrosine to p-hydroxyphenylacetaldehyde oxime in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench
stated in
The UDP-glucose:p-hydroxymandelonitrile-O-glucosyltransferase that catalyzes the last step in synthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor. Isolation, cloning, heterologous expression, and substrate specificity.
stated in
The biosynthesis of cyanogenic glucosides in higher plants. Identification of three hydroxylation steps in the biosynthesis of dhurrin in Sorghum bicolor (L.) Moench and the involvement of 1-ACI-nitro-2-(p-hydroxyphenyl)ethane as an intermediate.

Identifiers

Reaxys registry number
92611
1 reference
stated in
ChEBI
ChEBI ID
27826
language of work or name
English
title
(S)-4-hydroxymandelonitrile beta-D-glucoside (English)
retrieved
5 October 2016
ECHA Substance Infocard ID
100.007.163
1 reference
stated in
ECHA Substance Infocard database
ECHA Substance Infocard ID
100.007.163
retrieved
27 December 2018
title
(S)-(β-D-glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile (English)
quotation
CAS no.: 499-20-7 (English)
KNApSAcK ID
C00001442
1 reference
stated in
ChEBI
ChEBI ID
27826
language of work or name
English
title
(S)-4-hydroxymandelonitrile beta-D-glucoside (English)
retrieved
5 October 2016
KEGG ID
C05143
0 references
Freebase ID
/m/025z5g7
0 references
 
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