| Revision as of 14:05, 8 December 2010 editحسن علي البط (talk | contribs)Extended confirmed users, Pending changes reviewers19,940 edits removed Category:Naphthols; added Category:2-Naphthols using HotCat← Previous edit |
Latest revision as of 23:45, 5 August 2024 edit undoحسن علي البط (talk | contribs)Extended confirmed users, Pending changes reviewers19,940 edits removed Category:Hydroxyarenes; added Category:Hydroxynaphthoquinones using HotCat |
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{{chembox |
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| verifiedrevid = 379928547 |
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| Reference=<ref>''Merck Index'', 12th Edition, '''5406'''.</ref><ref> at Physical & Theoretical Chemistry Laboratory, ]</ref> |
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| verifiedrevid = 401250609 |
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| Reference =<ref>''Merck Index'', 12th Edition, '''5406'''.</ref><ref> {{Webarchive|url=https://web.archive.org/web/20051217032645/http://physchem.ox.ac.uk/MSDS/HY/2-hydroxy-1,4-naphthaquinone.html |date=2005-12-17 }} at Physical & Theoretical Chemistry Laboratory, ]</ref> |
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| ImageFile = HNQ.svg |
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| ImageFile = HNQ.svg |
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| ImageSize = 151 |
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| ImageSize = 151 |
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| ImageSize1 = 190 |
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| ImageSize1 = 190 |
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| ImageName1 = ball-and-stick model |
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| ImageName1 = ball-and-stick model |
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| IUPACName = 2-Hydroxy-1,4-naphthoquinone |
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| PIN = 2-Hydroxynaphthalene-1,4-dione |
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| OtherNames = Hennotannic acid<br>Natural Orange 6<br>C.I. 75480 |
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| OtherNames = 2-Hydroxy-1,4-naphthoquinone<br />Hennotannic acid<br />Natural Orange 6<br />C.I. 75480 |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 83-72-7 |
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| CASNo = 83-72-7 |
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| PubChem = 6755 |
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| Beilstein = 1565260 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| SMILES = O=C(C(O)=C1)C2=C(C=CC=C2)C1=O |
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| ChEBI = 44401 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 240963 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10430995 |
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| DrugBank = DB04744 |
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| EINECS = 201-496-3 |
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| Gmelin = 4828 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C10368 |
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| PubChem = 6755 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = TLH4A6LV1W |
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| InChI = 1/C10H6O3/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,12H |
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| InChIKey = CSFWPUWCSPOLJW-UHFFFAOYAK |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C10H6O3/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,12H |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = CSFWPUWCSPOLJW-UHFFFAOYSA-N |
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| SMILES = O=C(C(O)=C1)C2=C(C=CC=C2)C1=O |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>10</sub>H<sub>6</sub>O<sub>3</sub> |
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| Formula = C<sub>10</sub>H<sub>6</sub>O<sub>3</sub> |
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| MolarMass = 174.15 |
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| MolarMass = 174.15 g/mol |
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| Appearance = Yellow prisms |
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| Appearance = Yellow prisms |
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| Density = |
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| Density = |
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| MeltingPt = 195-196 °C (decomposition) |
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| MeltingPtC = 195 to 196 |
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| Solubility = almost insoluble <ref>http://msds.chem.ox.ac.uk/HY/2-hydroxy-1,4-naphthaquinone.html {{Dead link|date=August 2022}}</ref> |
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| Section3 = {{Chembox Hazards |
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| FlashPt = |
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| Autoignition = |
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| Hazards_ref=<ref>{{cite web |title=2-Hydroxy-1,4-naphthoquinone |url=https://pubchem.ncbi.nlm.nih.gov/compound/6755#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> |
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| RPhrases={{R36}} {{R37}} {{R38}} |
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| SPhrases={{S26}} {{S36}} {{S37}} {{S39}} |
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| GHSPictograms = {{GHS07}}{{GHS08}} |
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| GHSSignalWord = Warning |
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| LD50 = 100 mg/kg |
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| HPhrases = {{H-phrases|315|319|335}} |
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| PPhrases = {{P-phrases|201|202|261|264|270|271|280|281|301+312|302+352|304+340|305+351+338|308+313|312|330|332+313|337+313|362|403+233|405|501}} |
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| LD50 = 100 mg/kg |
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| Section8 = {{Chembox Related |
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| OtherFunctn = ] |
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| OtherFunction = ] |
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| Function = ]s |
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| OtherFunction_label = ]s |
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'''Lawsone''' ('''2-hydroxy-1,4-naphthoquinone'''), also known as '''hennotannic acid''', is a red-orange ] present in the leaves of the ] plant (''Lawsonia inermis'') as well as ] (''Impatiens balsamica'').<ref>{{cite journal|first=A. C.|last=Dweek|title=Natural ingredients for colouring and styling|journal=Int. J. Cosmetic Sci.|year=2002|volume=24|pages=287–302|doi=10.1046/j.1467-2494.2002.00148.x|pmid=18498522|issue=5}}</ref> Humans have used henna extracts containing lawsone as hair and skin ]s for more than 5000 years. Lawsone reacts chemically with the protein ] in skin and hair, in a process known as ], resulting in a strong permanent stain that lasts until the skin or hair is shed. Lawsone strongly absorbs ], and aqueous extracts can be effective ] ]s. Chemically, lawsone is similar to ], which is found in walnuts. |
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'''Lawsone''' ('''2-hydroxy-1,4-naphthoquinone'''), also known as '''hennotannic acid''', is a red-orange ] present in the leaves of the ] plant ('']''), for which it is named, as well as in the common walnut ('']'')<ref>{{ cite journal | first = A. C. | last = Dweck | title = Natural ingredients for colouring and styling | journal = International Journal of Cosmetic Science | year = 2002 | volume = 24 | issue = 5 | pages = 287–302 | doi = 10.1046/j.1467-2494.2002.00148.x | pmid = 18498522 }}</ref> and water hyacinth ('']'').<ref>{{cite journal |title= Effects of juglone and lawsone on oxidative stress in maize coleoptile cells treated with IAA |first1= Renata |last1= Kurtyka |first2= Wojciech |last2= Pokora |first3= Zbigniew |last3= Tukaj |first4= Waldemar |last4= Karcz |journal= AoB Plants |year= 2016 |volume= 8 |page= plw073 |doi= 10.1093/aobpla/plw073 |pmid= 27760740 |pmc= 5199135 }}</ref> Humans have used henna extracts containing lawsone as hair and skin ] for more than 5,000 years. Lawsone reacts chemically with the protein ] in skin and hair via a ], resulting in a strong permanent stain that lasts until the skin or hair is shed. Darker colored staining is due to more lawsone–keratin interactions occurring, which evidently break down as the concentration of lawsone decreases and the tattoo fades.<ref>Jordão, A.; Vargas, M.; Pinto, A.; da Silva, F.; Ferreira, V. Lawsone in organic synthesis. RSC Adv. 2015, 5, 67909-67943.</ref> Lawsone strongly absorbs ], and aqueous extracts can be effective ] agents and ]s. Lawsone is a ] derivative, an analog of ] containing one additional ring. |
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Lawsone isolation from ''Lawsonia inermis'' can be difficult due to its easily biodegradable nature. Isolation involves four steps: |
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== References == |
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# extraction with an extraction solution, usually NaOH |
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<references/> |
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# column filtration using a macroporous adsorption resin |
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# a rinse with ethanol to remove impurities, and finally |
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# freeze the product to isolate the lawsone powder, usually a yellow colored dust.<ref>Shuang, S.; Lei, Q.; Ting, Y.; Qifu, Y. Method for preparing lawsone from lawsonia inermis China Patent CN 103848732A, June 11, 2014.</ref> |
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During the rinse, the lawsone will be the bottom as it has such a high density and the chlorophyll molecules will all be on the top of the mixture.<ref>Gallo, F.; Multari, G.; Giambenedetti, M.; Federici, E. Chemical fingerprinting of Lawsonia inermis L. using HPLC, HPTLC, and densitometry. Phytochem. Anal. 2008, 19, 550-559.</ref> |
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Lawsone is hypothesized to undergo a reaction similar to ] in reactions with ]s.<ref name=":1">Jelly, R.; Lewis, S. W.;Lennard, C.; Lim, K. F.; Almog, J. Lawsone: a novel reagent for the detection of latent fingermarks on paper surfaces. Chem.Commun. 2008, 3513-3515</ref> Recent research has been conducted on lawsone's potential applications in the forensic science field. Since lawsone shows many similarities with ], the current reagent for latent fingerprint development, studies have been conducted to see if lawsone can be used in this field. As of now the research is inconclusive, but optimistic. Lawsone non-specifically targets primary amino acids, and displays photoluminescence with forensic light sources.<ref name=":1" /> It has a characteristic purple/brown coloration as opposed to the purple/blue associated with ninhydrin.<ref>Jelly, R.; Lewis, S. W.; Lennard, C.; Lim, K. F.; Almog, J. Lawsone: a novel reagent for the detection of latent fingermarks on paper surfaces. Chem. Commun. 2008, 3513-3515.</ref> |
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== External links == |
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Lawsone shows promise as a reagent for fingerprint detection because of its photoluminescence maximized at 640 nm, which is high enough that it avoids background interference common for ninhydrin.<ref>Thomas, P.; Farrugia, K. An investigation into the enhancement of fingermarks in blood on paper with ] and lawsone. Sci. Justice 2013, 53, 315-320.</ref> |
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== Related compounds == |
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The naphthoquinones ] and ] are some of the active compounds in '']'' leaves.<ref>{{ cite journal |author1=Sakunphueak, A. |author2=Panichayupakaranant, P. | title = Simultaneous determination of three naphthoquinones in the leaves of ''Impatiens balsamina'' L. by reversed‐phase high‐performance liquid chromatography | journal = Phytochemical Analysis | year = 2010 | volume = 21 | issue = 5 | pages = 444–50 | pmid = 20931623 | doi = 10.1002/pca.1216 }}</ref> ] is a ] used as a brown dye. |
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== References == |
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