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Revision as of 18:09, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 443352206 of page 4-Chloroindole-3-acetic_acid for the Chem/Drugbox validation project (updated: 'CASNo').  Latest revision as of 20:58, 26 November 2024 edit Marbletan (talk | contribs)Extended confirmed users5,415 edits no longer a stub 
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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.}}
{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 443350876
| Watchedfields = changed
⚫ |ImageFile=4-chloroindole-3-acetic acid.png
⚫ | verifiedrevid = 477221306
⚫ |ImageSize=200px
|IUPACName=2-(4-chloro-1''H''-indol-3-yl)acetic acid | ImageFile = 4-chloroindole-3-acetic acid.png
⚫ | ImageSize = 150
|OtherNames=
⚫ | ImageAlt = Skeletal formula of 4-chloroindole-3-acetic acid
⚫ |Section1= {{Chembox Identifiers
| ImageSize1 = 165
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ImageAlt1 = Space-filling model of the 4-chloroindole-3-acetic acid molecule
| PIN = (4-Chloro-1''H''-indol-3-yl)acetic acid <!-- the locant ‘2’ for acetic acid is not cited -->
| OtherNames = 2-(4-Chloro-1''H''-indol-3-yl)acetic acid
⚫ |Section1={{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 90727 | ChemSpiderID = 90727
| InChI = 1/C10H8ClNO2/c11-7-2-1-3-8-10(7)6(5-12-8)4-9(13)14/h1-3,5,12H,4H2,(H,13,14) | InChI = 1/C10H8ClNO2/c11-7-2-1-3-8-10(7)6(5-12-8)4-9(13)14/h1-3,5,12H,4H2,(H,13,14)
| InChIKey = WNCFBCKZRJDRKZ-UHFFFAOYAY | InChIKey = WNCFBCKZRJDRKZ-UHFFFAOYAY
| SMILES1 = Clc1cccc2c1c(cn2)CC(=O)O | SMILES = Clc1cccc2c1c(c2)CC(=O)O
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 309993 | ChEMBL = 309993
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WNCFBCKZRJDRKZ-UHFFFAOYSA-N | StdInChIKey = WNCFBCKZRJDRKZ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|changed|??}}
| CASNo = <!-- blanked - oldvalue: 2519-61-1 -->
| CASNo=2519-61-1
⚫ | PubChem=100413
| ChEBI_Ref = {{ebicite|correct|EBI}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = RF78HU5XXV
⚫ | PubChem=100413
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 20339 | ChEBI = 20339
⚫ }}
| SMILES=OC(CC1=CNC2=CC=CC(Cl)=C21)=O
⚫ |Section2={{Chembox Properties
⚫ }}
⚫ | C=10 | H=8 | Cl=1 | N=1 | O=2
⚫ |Section2= {{Chembox Properties
| Appearance=
⚫ | C=10|H=8|Cl=1|N=1|O=2
| Appearance= | Density=
| Density= | MeltingPt=
| MeltingPt= | BoilingPt=
| BoilingPt= | Solubility=
| Solubility=
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}

'''4-Chloroindole-3-acetic acid''' ('''4-Cl-IAA''') is an organic compound that functions as a ].<ref>{{cite journal |last1=Reinecke |first1=Dennis M. |year=1999 |title=4-Chloroindole-3-acetic acid and plant growth |journal=Plant Growth Regulation |volume=27 |issue=1 |pages=3–13 |doi=10.1023/A:1006191917753 |s2cid=23683065 |issn=0167-6903}}</ref>

==Synopsis==
It is a member of the class of compounds known as ]s and a chlorinated analogue of the more common ] (IAA) auxin. 4-Cl-IAA is found in the seeds of a variety of plants, particularly ]s such as peas and broad beans.<ref name=pless>{{cite journal |doi=10.1104/pp.74.2.320 |author1=Pless, Tanja |author2=Boettger, Michael |author3=Hedden, Peter |author4=Graebe, Jan |title=Occurrence of 4-Cl-indoleacetic acid in broad beans and correlation of its levels with seed development |journal=Plant Physiology |year=1984 |volume=74 |issue=2 |pages=320–3 |pmid=16663416 |pmc=1066676}}</ref><ref name=ernst>{{cite journal |author1=Ernstsen, Arild |author2=Sandberg, Goeran |title=Identification of 4-chloroindole-3-acetic acid and indole-3-aldehyde in seeds of ''Pinus sylvestris'' |journal=Physiologia Plantarum |year=1986 |volume=68 |issue=3 |pages=511–18 |doi=10.1111/j.1399-3054.1986.tb03390.x}}</ref><ref name=kata>{{cite journal |author1=Katayama, Masato |author2=Thiruvikraman, Singanallore V. |author3=Marumo, Shingo |title=Identification of 4-chloroindole-3-acetic acid and its methyl ester in immature seeds of ''Vicia amurensis'' (the tribe ''Vicieae''), and their absence from three species of ''Phaseoleae'' |journal=Plant and Cell Physiology |year=1987 |volume=28 |issue=2 |pages=383–386 |issn=0032-0781 |url=http://pcp.oxfordjournals.org/content/28/2/383.abstract |archive-url=https://archive.today/20131016172228/http://pcp.oxfordjournals.org/content/28/2/383.abstract |url-status=dead |archive-date=16 October 2013 |access-date=16 October 2013}}</ref><ref name=magnus>{{cite journal |last1=Magnus |first1=Volker |last2=Ozga |first2=Jocelyn A. |last3=Reinecke |first3=Dennis M. |last4=Pierson |first4=Gerald L. |last5=Larue |first5=Thomas A. |last6=Cohen |first6=Jerry D. |last7=Brenner |first7=Mark L |title=4-chloroindole-3-acetic and indole-3-acetic acids in ''Pisum sativum'' |journal=Phytochemistry |year=1997 |volume=46 |issue=4 |pages=675–681 |doi=10.1016/S0031-9422(97)00229-X|doi-access=free }}</ref> In one study it is written that the substance is "mainly found in reproductive structures" and "is thought to be restricted to members of the leguminous tribe '']'', specifically "the genera '']'', '']'', '']'', '']'', and '']''".<ref name=lam/> In ], 4-Cl-IAA biosynthesis diverges from IAA biosynthesis when the amino acid ] is chlorinated to form 4-chlorotryptophan (4-Cl-Trp); the biosynthesis of 4-Cl-IAA then precedes parallel to that of IAA.<ref>{{cite journal | last1 = Tivendale | first1 = N.D. | last2 = Davidson | first2 = S. E. | last3 = Davies | first3 = N. W. | last4 = Smith | first4 = J. A. | last5 = Dalmais | first5 = M. | last6 = Bendahmane | first6 = A. I. | last7 = Quittenden | first7 = L. J. | last8 = Sutton | first8 = L. | last9 = Bala | first9 = R. K. | last10 = Signor | first10 = C. Le | last11 = Thompson | first11 = R. | last12 = Horne | first12 = J. | last13 = Reid | first13 = J. B. | last14 = Ross | first14 = J. J. | year = 2012 | title = Biosynthesis of the Halogenated Auxin, 4-Chloroindole-3-Acetic Acid | journal = Plant Physiology | volume = 159 | issue = 3| pages = 1055–1063 | doi = 10.1104/pp.112.198457 | pmid = 22573801 | pmc = 3387693 | doi-access = free }}</ref>

Engvild hypothesized in 1996 that 4-Cl-IAA may be a "death hormone" that maturing seeds use to trigger death of the parent plant by mobilizing nutrients to be stored in the seed.<ref>{{cite journal |title=Herbicidal activity of 4-chloroindoleacetic acid and other auxins on pea, barley and mustard |author =Engvild, Kjeld C.|journal=Physiologia Plantarum |year=1996 |volume=96 |issue=2 |pages=333–337 |doi=10.1111/j.1399-3054.1996.tb00222.x}}</ref>

Lam et al found the substance in the seeds of '']'', '']'', and three species of '']''.<ref name=lam>{{cite journal |pmid=25971549|pmc=4741347|year=2015|last1=Lam|first1=H. K.|title=Evidence That Chlorinated Auxin is Restricted to the Fabaceae but Not to the Fabeae|journal=Plant Physiology|volume=168|issue=3|pages=798–803|last2=McAdam|first2=S. A.|last3=McAdam|first3=E. L.|last4=Ross|first4=J. J.|doi=10.1104/pp.15.00410}}</ref>

==References==
{{reflist}}

{{DEFAULTSORT:Chloro-3-indoleacetic acid, 4-}}

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