(-)-Alkannin
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(-)-Alkannin
structure -
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CAS No:
517-88-4
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Formula:
C16H16O5
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Chemical Name:
(-)-Alkannin
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Synonyms:
1,4-Naphthalenedione,5,8-dihydroxy-2-[(1S)-1-hydroxy-4-methyl-3-penten-1-yl]-;1,4-Naphthoquinone,5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-,(-)-;Alkannin;1,4-Naphthalenedione,5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-,(S)-;1,4-Naphthalenedione,5,8-dihydroxy-2-[(1S)-1-hydroxy-4-methyl-3-pentenyl]-;5,8-Dihydroxy-2-[(1S)-1-hydroxy-4-methyl-3-penten-1-yl]-1,4-naphthalenedione;C.I. 75530;Anchusin;C.I. Natural Red 20;Alkanet extract;Anchusa acid;Alkanna red;(-)-Alkannin;NSC 94524
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CAS No:
Description
Alkannin, found in Alkanna tinctoria, is used as a food coloring. Alkannin shows anticancer activity, arrests cell cycle, and induces apoptosis. Alkannin improves hepatic inflammation in a Rho-kinase pathway[1][2][3].
Alkannin is a hydroxy-1,4-naphthoquinone.
Characteristics
94.83000
2.12040
1.373g/cm3
149 °C
567.4ºC at 760mmHg
311ºC
1.642
LD50 in male, female mice, rats (g/kg): 3.0 ± 1.0; 3.1 ± 0.1; >1.0 orally (Majlathova)
(-)-Alkannin Use and Manufacturing
Alkannin is a natural dye that is obtained from the extracts of plants from the borage family Alkanna tinctoria that are found in the south of France. The dye is used as a food coloring and in cosmetics. It is used as a red-brown food additive in regions such as Australia, and is designated in Europe as the E number E103, but is no longer approved for use.The chemical structure as a naphthoquinone derivative was first determined by Brockmann in 1936. Alkannin has a deep red color in a greasy or oily environment and a violet color in an alkaline environment.The enzyme 4-hydroxybenzoate geranyltransferase utilizes geranyl diphosphate and 4-hydroxybenzoate to produce 3-geranyl-4-hydroxybenzoate and diphosphate. These compounds are then used to form alkannin.Alkannin is an antioxidant and has an antimicrobial effect against Staphylococcus aureus and Staphylococcus epidermidis. It is also known to have wound healing, antitumor, and antithrombotic properties.Shikonin is also found in the Chinese herbal medicine plant Lithospermum erythrorhizon, the red-root gromwell, (紫草 zicao, Pinyin: zǐcǎo). The dried root is a Chinese herbal medicine with various antiviral and biological activities, including inhibition of human immunodeficiency virus type 1 (HIV-1).
Cosmetics -> Tonic
Computed Properties
Molecular Weight:288.29
XLogP3:3
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:288.09977361
Monoisotopic Mass:288.09977361
Topological Polar Surface Area:94.8
Heavy Atom Count:21
Complexity:501
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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