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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
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.