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alkannin
Sign in to saveAlso known as alkanet extract, C.I. Natural red 20, Anchusaic acid, Anchusin
Alkannin is a natural dye that is obtained from the extracts of the plant dyer's alkanet (Alkanna tinctoria) which is found in the Mediterranean region. The dye is used as a food coloring and in cosmetics; within the European E number schedule, it is numbered E103. It is used as a red-brown food additive in regions such as Australia. Alkannin is deep red in an acid and blue in an alkaline environment. The chemical structure as a naphthoquinone derivative was first determined by Hans Brockmann in 1936. The (R)-enantiomer of alkannin is known as shikonin, and the racemic mixture of the two is kn
In the Vinony graph
Vinony's link graph records 21 inbound references to alkannin, and connects out to mass density, Wayback Machine and digital object identifier.
It is catalogued under topics including 1,4-Naphthoquinones, 3-Hydroxypropenals within hydroxyquinones and Alkene derivatives.
Vinony links it to 13 Wikipedia language editions.
Chemical data
- Formula
- C16H16O5
- Molecular weight
- 288.29 g/mol
- IUPAC name
- 5,8-dihydroxy-2-[(1S)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione
- SMILES
- CC(=CC[C@@H](C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)O)C
- InChIKey
- NEZONWMXZKDMKF-JTQLQIEISA-N
- XLogP
- 3
- Polar surface area
- 94.8 Ų
- H-bond donors
- 3
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 288.1
- Has use
- food coloring
Show 6 more facts
- Commons category
- Alkannin
- found in taxon
- Arnebia decumbens
- chemical formula
- C₁₆H₁₆O₅
- isomeric SMILES
- CC(=CC[C@@H](C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)O)C
- canonical SMILES
- CC(=CCC(C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)O)C
- natural product of taxon
- Alkanna tinctoria
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Biosynthesis
- Research
- References
Alkannin is a natural dye that is obtained from the extracts of the plant dyer's alkanet (Alkanna tinctoria) which is found in the Mediterranean region. The dye is used as a food coloring and in cosmetics; within the European E number schedule, it is numbered E103. It is used as a red-brown food additive in regions such as Australia. Alkannin is deep red in an acid and blue in an alkaline environment. The chemical structure as a naphthoquinone derivative was first determined by Hans Brockmann in 1936. The (R)-enantiomer of alkannin is known as shikonin, and the racemic mixture of the two is known as shikalkin.
== Biosynthesis == The enzyme 4-hydroxybenzoate geranyltransferase utilizes geranyl diphosphate and 4-hydroxybenzoic acid to produce 3-geranyl-4-hydroxybenzoic acid and diphosphate. These compounds are then used to form alkannin.
Excerpted from Wikipedia’s “alkannin” article, available under the CC BY-SA 4.0 licence.