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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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| Watchedfields = changed |
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| verifiedrevid = 413308298 |
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| verifiedrevid = 477247480 |
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| ImageFile = Alkannin.svg |
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| ImageFile = Alkannin v2.svg |
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| ImageAlt = Skeletal formula of alkannin |
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| ImageSize = 200px |
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| ImageFile1 = Alkannin 3D spacefill.png |
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| IUPACName = 5,8-Dihydroxy-2-naphthalene-1,4-dione |
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| ImageAlt1 = Space-filling model of the alkannin molecule |
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| OtherNames = C.I. Natural Red 20; Alkanet extract |
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| PIN = 5,8-Dihydroxy-2-naphthalene-1,4-dione |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = {{Unbulleted list|C.I. Natural red 20|Alkanet extract|Anchusaic acid|Anchusin}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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|Section1={{Chembox Identifiers |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C10292 |
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| KEGG = C10292 |
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| InChI = 1/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3/t10-/m0/s1 |
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| InChI = 1/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3/t10-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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<!-- | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = NEZONWMXZKDMKF-JTQLQIEIBC |
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| StdInChIKey = NEZONWMXZKDMKF-JTQLQIEIBC (comment: Chembox cannot have two StdInCHIkey values. 24 Nov 2014 --> |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3/t10-/m0/s1 |
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| StdInChI = 1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3/t10-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = NEZONWMXZKDMKF-JTQLQIEISA-N |
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| StdInChIKey = NEZONWMXZKDMKF-JTQLQIEISA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 517-88-4 --> |
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| CASNo = 517-88-4 |
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| UNII_Ref = {{cascite|correct|CAS}} |
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| PubChem = 72521 |
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| UNII = 075CRZ9995 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PubChem = 72521 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 65430 |
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| ChemSpiderID = 65430 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 28457 |
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| ChEMBL = 28457 |
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| SMILES = O=C\2c1c(O)ccc(O)c1C(=O)/C(=C/2)(O)CC=C(C)C |
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| SMILES = O=C\2c1c(O)ccc(O)c1C(=O)/C(=C/2)(O)CC=C(C)C |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Reference=<ref>'']'', 11th Edition, '''243'''</ref> |
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| Properties_ref = <ref>'']'', 11th Edition, '''243'''</ref> |
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| Formula = {{Chem|C|16|H|16|O|5}} |
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| C=16|H=16|O=5 |
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| Appearance = Red-brown crystalline prisms |
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| MolarMass = 288.29 g/mol |
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| Density = 1.15 g/mL |
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| Appearance = Red-brown crystalline prisms |
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| Density = |
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| MeltingPtC = 149 |
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| MeltingPtC = 149 |
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| BoilingPtC = 567 |
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| Solubility = Sparingly soluble |
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| BoilingPt = |
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| Solubility = Sparingly soluble |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| LD50 = 3.0 g/kg (mice) |
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| Autoignition = |
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| LD50 = 3.0 g/kg (mice) |
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'''Alkannin''' is a ] that is obtained from the extracts of the plant ] (''Alkanna tinctoria'') which is found in the ]. The dye is used as a ] and in cosmetics; within the European ] schedule, it is numbered '''E103'''. It is used as a red-brown ] in regions such as Australia.<ref> {{Webarchive|url=https://web.archive.org/web/20110406040011/http://www.foodstandards.gov.au/_srcfiles/Additives%20alpha.pdf |date=2011-04-06 }}, ]</ref> Alkannin is deep red in an acid and blue in an alkaline environment.<ref>{{cite book | chapter = Alkanet | url = http://www.henriettesherbal.com/eclectic/usdisp/alkanna.html | title = Dispensatory of the United States of America | date = 1918 | editor = Joseph P. Remington and Horatio C. Wood }}</ref> The chemical structure as a ] derivative was first determined by Hans Brockmann in 1936.<ref>{{cite journal | doi = 10.1002/jlac.19365210102 | author = H. Brockmann | title = Die Konstitution des Alkannins, Shikonins und Alkannans | journal = Justus Liebigs Ann. Chem. | year = 1936 | volume = 521 | issue = 1 | pages = 1–47}}</ref> The (''R'')-] of alkannin is known as '''shikonin''', and the ] of the two is known as '''shikalkin'''.<ref>{{cite book | title = Dictionary of Food Compounds | page = 478 | author = Shmuel Yannai | publisher = CRC Press | date = 2012}}</ref><ref name=Nicolaou>{{cite journal | doi = 10.1002/(SICI)1521-3773(19990201)38:3<270::AID-ANIE270>3.0.CO;2-0 | title = The Chemistry and Biology of Alkannin, Shikonin, and Related Naphthazarin Natural Products | author = Vassilios P. Papageorgiou |author2=Andreana N. Assimopoulou |author3=Elias A. Couladouros |author4=David Hepworth | author5-link = K. C. Nicolaou |author5=K. C. Nicolaou |display-authors=3| journal = Angew. Chem. Int. Ed. | year = 1999 | volume = 38 | pages = 270–300 | issue = 3| pmid = 29711637 }}</ref> |
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== Biosynthesis == |
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The enzyme ] utilizes ] and ] to produce ] and diphosphate. These compounds are then used to form alkannin.<ref name="Nicolaou" /> |
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== Research == |
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Because the root bark (cork layers) of ''Alkanna tinctoria'' contains large amounts of red ] pigments, including alkannin, the roots of these plants are red-purple. When extracted from fresh tissues, the pigment gradually darkens over several days, finally forming black precipitates, which are thought to be polymers.<ref name="Kazufumi">{{cite journal | doi = 10.5511/plantbiotechnology.17.0823a | title = ''Lithospermum erythrorhizon'' cell cultures: Present and future aspects | date = 2017 | last1 = Yazaki | first1 = Kazufumi | journal = Plant Biotechnology | volume = 34 | issue = 3 | pages = 131–142 | pmid = 31275019 | pmc = 6565996 }}</ref> |
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== References == |
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