| Revision as of 15:17, 17 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 405878172 of page Geranic_acid for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CASNo'). |
Latest revision as of 13:50, 14 April 2024 edit Ristando (talk | contribs)84 edits Added NFPA704, pictograms, LD50, flash point, SDS |
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{{distinguish|Germanic acid}} |
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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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| Verifiedfields = changed |
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| Watchedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 400099276 |
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| verifiedrevid = 461119690 |
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| Name = Geranic acid |
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| Name = Geranic acid |
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| ImageFile = Geranic acid.png |
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| ImageFile = Geranic acid.png |
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| ImageSize = 220 |
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| ImageSize = 220 |
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| ImageName = Skeletal formula |
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| ImageAlt = Skeletal formula of geranic acid |
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| ImageFile1 = Geranic-acid-3D-balls.png |
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| ImageFile1 = Geranic acid 3D ball.png |
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| ImageSize1 = 240 |
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| ImageSize1 = 240 |
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| ImageName1 = Ball-and-stick model |
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| ImageAlt1 = Ball-and-stick model of the geranic acid molecule |
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| IUPACName = 3,7-Dimethyl-2,6-octadienoic acid |
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| PIN = (2''E'')-3,7-Dimethylocta-2,6-dienoic acid |
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| OtherNames = Geranic acid |
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| OtherNames = Geranic acid |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| SMILES = O=C(O)/C=C(/CC\C=C(/C)C)C |
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| SMILES = O=C(O)/C=C(/CC\C=C(/C)C)C |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4439624 |
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| ChemSpiderID = 4439624 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 67264 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 170190 |
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| ChEMBL = 170190 |
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| PubChem = 5275520 |
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| PubChem = 5275520 |
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| InChI = 1/C10H16O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,7H,4,6H2,1-3H3,(H,11,12)/b9-7+ |
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| InChIKey = ZHYZQXUYZJNEHD-VQHVLOKHBQ |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C10H16O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,7H,4,6H2,1-3H3,(H,11,12)/b9-7+ |
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| StdInChI = 1S/C10H16O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,7H,4,6H2,1-3H3,(H,11,12)/b9-7+ |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = ZHYZQXUYZJNEHD-VQHVLOKHSA-N |
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| StdInChIKey = ZHYZQXUYZJNEHD-VQHVLOKHSA-N |
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| CASNo_Ref = {{cascite|changed|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 459-80-3 --> |
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| RTECS = |
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| CASNo = 4698-08-2 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = 10797G3M5Y |
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| RTECS = |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=10 | H=16 | O=2 |
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| Formula = C<sub>10</sub>H<sub>16</sub>O<sub>2</sub> |
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| MolarMass = 168.24 g/mol |
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| Appearance = Oily liquid |
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| Density = 0.97 g/cm<sup>3</sup> |
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| Appearance = Oily liquid |
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| Solubility = |
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| Density = 0.97 g/cm<sup>3</sup> |
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| Solubility = |
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| MeltingPt = |
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| BoilingPtC = 249 to 251 |
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| MeltingPt = |
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| BoilingPt_notes = |
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| BoilingPt = 249-251 °C (522.15-524.15 K) |
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| pKa = |
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| pKa = |
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| Viscosity = |
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| Viscosity = |
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| Section3 = {{Chembox Structure |
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|Section3={{Chembox Structure |
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| Coordination = |
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| Coordination = |
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| CrystalStruct = |
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| CrystalStruct = |
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| Dipole = |
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| Dipole = |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| MainHazards = |
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| MainHazards = |
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| GHSSignalWord = Warning |
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| FlashPt = |
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| FlashPtC = 133 |
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| GHSPictograms = {{GHS07}} |
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| NFPA-H = 2 |
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| NFPA-F = 1 |
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| NFPA-I = 0 |
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| LD50 = 3700 mg/kg (oral, rat) |
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| ExternalSDS = |
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| Section8 = {{Chembox Related |
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|Section8={{Chembox Related |
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| Function = ]s |
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| OtherFunction_label = ]s |
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| OtherFunctn = ] |
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| OtherFunction = ], ] |
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| OtherCpds = ]<br />] |
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| OtherCompounds = ]<br />] |
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'''Geranic acid''', or 3,7-dimethyl-2,6-octadienoic acid, is a ] used by some organisms.<ref>, pherobase.com</ref> It is a ] of ]. |
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==Pharmacology== |
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'''Choline geranate''' (also described as '''Choline''' And '''Geranic acid''', or '''CAGE''') has been developed as a novel biocompatible antiseptic material capable of penetrating skin and aiding the transdermal delivery of co-administered antibiotics. |
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The antibacterial properties of CAGE were analyzed against 24 and 72 hour old biofilms of 11 clinically isolated ESKAPE pathogens (defined as Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumanii, Pseudomonas aeruginosa, and Enterobacter sp, respectively), including multidrug resistant (MDR) isolates. |
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CAGE was observed to eradicate in vitro biofilms at concentrations as low as 3.56 mM (0.156% v:v) in as little as 2 hours, which represents both an improved potency and rate of biofilm eradication relative to that reported for most common standard-of-care topical antiseptics in current use. In vitro time-kill studies on 24 hour old Staphylococcus aureus biofilms indicate that CAGE exerts its antibacterial effect upon contact and a 0.1% v:v solution reduced biofilm viability by over three orders of magnitude (a 3log10 reduction) in 15 minutes. |
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Furthermore, disruption of the protective layer of exopolymeric substances in mature biofilms of Staphylococcus aureus by CAGE (0.1% v:v) was observed in 120 minutes. Insight into the mechanism of action of CAGE was provided with molecular modeling studies alongside in vitro antibiofilm assays. The geranate ion and geranic acid components of CAGE are predicted to act in concert to integrate into bacterial membranes, affect membrane thinning and perturb membrane homeostasis. <ref>{{Cite journal|pmid = 31527873|year = 2019|last1 = Greene|first1 = J. R.|last2 = Merrett|first2 = K. L.|last3 = Heyert|first3 = A. J.|last4 = Simmons|first4 = L. F.|last5 = Migliori|first5 = C. M.|last6 = Vogt|first6 = K. C.|last7 = Castro|first7 = R. S.|last8 = Phillips|first8 = P. D.|last9 = Baker|first9 = J. L.|last10 = Lindberg|first10 = G. E.|last11 = Fox|first11 = D. T.|last12 = Del Sesto|first12 = R. E.|last13 = Koppisch|first13 = A. T.|title = Scope and efficacy of the broad-spectrum topical antiseptic choline geranate|journal = PLOS ONE|volume = 14|issue = 9|pages = e0222211|doi = 10.1371/journal.pone.0222211|pmc = 6748422|bibcode = 2019PLoSO..1422211G|doi-access = free}}</ref> |
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==References== |
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{{reflist}} |
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{{alkene-stub}} |