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Revision as of 13:50, 9 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEBI').← Previous edit Latest revision as of 23:22, 13 April 2024 edit undo98.123.38.211 (talk)No edit summary 
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{{chembox {{chembox
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 415663454 | verifiedrevid = 443873074
| ImageFile=Indole-3-butyric_acid.svg | ImageFile=Indole-3-butyric acid structure.svg
| IUPACName = 1H-Indole-3-butanoic acid | PIN = 4-(1''H''-Indol-3-yl)butanoic acid
| OtherNames = indole-3-butyric acid<br />3-indolebutyric acid<br />indolebutyric acid<br />IBA | OtherNames = 1''H''-Indole-3-butanoic acid<br/>Indole-3-butyric acid<br/>3-Indolebutyric acid<br/>Indolebutyric acid<br/>IBA
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | DrugBank = DB02740
⚫ | CASNo = 133-32-4
| Beilstein = 171120
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 33070 | ChEBI = 33070
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | SMILES = O=C(O)CCCc2c1ccccc1nc2
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8298 | ChemSpiderID = 8298
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫ | DrugBank = DB02740
| EC_number = 205-101-5
| Gmelin = 143637
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C11284 | KEGG = C11284
⚫ | InChI = 1/C12H13NO2/c14-12(15)7-3-4-9-8-13-11-6-2-1-5-10(9)11/h1-2,5-6,8,13H,3-4,7H2,(H,14,15)
⚫ | InChIKey = JTEDVYBZBROSJT-UHFFFAOYAT
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 582878 | ChEMBL = 582878
⚫ | RTECS = NL5250000
| PubChem = 8617
| UNII = 061SKE27JP
⚫ | InChI = 1/C12H13NO2/c14-12(15)7-3-4-9-8-13-11-6-2-1-5-10(9)11/h1-2,5-6,8,13H,3-4,7H2,(H,14,15)
⚫ | InChIKey = JTEDVYBZBROSJT-UHFFFAOYAT
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H13NO2/c14-12(15)7-3-4-9-8-13-11-6-2-1-5-10(9)11/h1-2,5-6,8,13H,3-4,7H2,(H,14,15) | StdInChI = 1S/C12H13NO2/c14-12(15)7-3-4-9-8-13-11-6-2-1-5-10(9)11/h1-2,5-6,8,13H,3-4,7H2,(H,14,15)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JTEDVYBZBROSJT-UHFFFAOYSA-N | StdInChIKey = JTEDVYBZBROSJT-UHFFFAOYSA-N
⚫ | SMILES = O=C(O)CCCc1cc2ccccc12
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo = 133-32-4
⚫ | RTECS = NL5250000
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=12 | H = 13 | N = 1 | O = 2 | C=12 | H=13 | N=1 | O=2
| Appearance = white to light yellow crystals | Appearance = White to light yellow crystals
| Density = 1.252g/cm<sup>3</sup> | Density = 1.252 g/cm<sup>3</sup>
| Solubility = | Solubility =
| MeltingPtC = 125 | MeltingPtC = 125
| BoilingPt = decomposes | BoilingPt = Decomposes
| pKa = | pKa =
| pKb = | pKb =
| Viscosity = | Viscosity =
}} }}
| Section3 = {{Chembox Structure |Section3={{Chembox Structure
| CrystalStruct = ] | CrystalStruct = ]
| Dipole = | Dipole =
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| MainHazards = | MainHazards =
| FlashPt = 211.8°C | FlashPtC = 211.8
| RPhrases = {{R25}} {{R36/37/38}} | GHSPictograms = {{GHS06}}{{GHS07}}
| GHSSignalWord = Danger
| SPhrases = {{S26}} {{S28}} {{S36/37/39}} {{S38}} {{S45}}
| HPhrases = {{H-phrases|301|315|319|335}}
| PPhrases = {{P-phrases|261|264|270|271|280|301+310|302+352|304+340|305+351+338|312|321|330|332+313|337+313|362|403+233|405|501}}
}} }}
| Section8 = {{Chembox Related |Section8={{Chembox Related
| OtherFunction_label =
| Function =
| OtherFunctn = ]<br />] | OtherFunction = ]<br />]
}} }}
}} }}


'''Indole-3-butyric acid''' (1H-Indole-3-butanoic acid, IBA) is a white to light-yellow crystalline solid, with the molecular formula C<sub>12</sub>H<sub>13</sub>NO<sub>2</sub>. It melts at 125 °C in atmospheric pressure and decomposes before boiling. '''Indole-3-butyric acid''' ('''1''H''-indole-3-butanoic acid''', '''IBA''') is a white to light-yellow crystalline solid, with the molecular formula C<sub>12</sub>H<sub>13</sub>NO<sub>2</sub>. It melts at 125°C in atmospheric pressure and decomposes before boiling. IBA is a ] in the ] family and is an ingredient in many commercial horticultural ] products.


==Plant hormone== ==Plant hormone==
⚫ Since IBA is not completely soluble in water, it is typically ] in 75% or purer ] for use in plant rooting, making a solution of between 10,000 and 50,000 ]. This alcohol solution is then diluted with ] to the desired <!-- "required" would be a nice fact but it needs specifying -->]. IBA is also available as a ], which is soluble in water. The solution should be kept in a cool, dark place for best results.
IBA is a ] in the ] family and is an ingredient in many commercial horticultural plant rooting products.


This compound had been thought to be strictly ]; however, it was reported that the compound was isolated from leaves and seeds of maize and other species. In maize, IBA has been shown to be ]d in vivo from ] and other compounds as precursors.<ref>{{cite news| author = Ludwig-Müller, J.| title = Indole-3-butyric acid in plant growth and development | year = 2000| journal = Plant Growth Regulation| volume = 32 | issue = 2–3}}</ref> This chemical may also be extracted from any of the Salix (]) genus.<ref>{{cite book| author = William G. Hopkins| title = Introduction to plant physiology| year = 1999| publisher = Wiley| isbn = 978-0-471-19281-7| url-access = registration| url = https://archive.org/details/introductiontopl0002hopk}}</ref>
⚫ Since IBA is not soluble in water), for use in plant rooting, it is typically ] , making a solution of between 10,000 to 50,000 ], in 75% or purer ], and then the alcohol solution is diluted to the desired <!-- "required" would be a nice fact but it needs specifying -->] using ]. IBA is also available as a ], which is soluble in water. The solution should be kept in a cool, dark place for best results.


==Plant tissue culture==
This compound had been thought to be strictly ]; however, it was reported that the compound was isolated from leaves and seeds of maize and other species. This chemical may also be extracted from any of the salix (willow) genus. <ref>William. G.Hopkins(1999). ''Introduction to Plant Physiology.'' John Wiley and Sons. ISBN 0-471-19281-3</ref>
In plant tissue culture IBA and other auxins are used to initiate root formation in vitro in a procedure called ]. Micropropagation of plants is the process of using small samples of plants called explants and causing them to undergo growth of differentiated or undifferentiated cells. In connection with ] like ], auxins like IBA can be used to cause the formation of masses of undifferentiated cells called ]. Callus formation is often used as a first step process in micropropagation where the callus cells are then caused to form other tissues such as roots by exposing them to certain hormones like auxins that produce roots. The process of callus to root formation is called indirect organogenesis whereas if roots are formed from the explant directly it is called direct organogenesis.<ref>{{cite news| author = Bridgen, M.P, Masood, Z.H. and Spencer-Barreto, M. | title = A laboratory exercise to demonstrate direct and indirect shoot organogenesis from leaves of Torenia fournieri. | year = 1992| journal = HortTechnology | pages = 320–322}}</ref>

In a study of '']'', the effect of three different auxins, IBA, ] and ] were examined to determine the relative effect of each auxin on root formation. According to the result for the species, IBA was shown to produce a higher yield of roots compared to the other auxins.<ref>{{cite news| author = Rout, G.R.| title = Effect of auxins on adventitious root development from single node cuttings of Camellia sinensis (L.) Kuntze and associated biochemical changes| date = Feb 2006| journal = Plant Growth Regulation| volume = 48 | issue = 2}}</ref> The effect of IBA is in concurrence with other studies where IBA is the most commonly used auxin for root formation.<ref>{{cite news|author1=Pooja Goyal |author2=Sumita Kachhwaha |author3=S. L. Kothari | title = Micropropagation of Pithecellobium dulce (Roxb.) Benth—a multipurpose leguminous tree and assessment of genetic fidelity of micropropagated plants using molecular markers| date = April 2012| journal = Physiol Mol Biol Plants| volume = 18 | issue = 2}}</ref>

==Mechanism==
Although the exact method of how IBA works is still largely unknown, genetic evidence has been found that suggests that IBA may be converted into IAA through a similar process to ] of ]. The conversion of IBA to IAA then suggests that IBA works as a storage sink for IAA in plants.<ref>{{cite news| author = Zolman, B.K., Martinez, N., Millius, A., Adham, A.R., Bartel, B| title = Identification and characterization of Arabidopsis indole-3-butyric acid response mutants defective in novel peroxisomal enzymes| year = 2008| journal = Genetics| volume = 180 | issue = 1}}</ref> There is other evidence that suggests that IBA is not converted to IAA but acts as an auxin on its own.<ref>{{cite news| author = Ludwig-Müller, J.| title = Indole-3-butyric acid in plant growth and development | year = 2000| journal = Plant Growth Regulation| volume = 32 | issue = 2–3}}</ref>


==References== ==References==
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==External links== ==External links==
{{commons category inline|Indolebutyric acid}}
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