| Revision as of 11:41, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 464352380 of page Prenol for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 19:24, 10 November 2024 edit Smokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,476 edits →Uses: ref |
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{{Chembox |
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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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| Watchedfields = changed |
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{{chembox |
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| verifiedrevid = 464213986 |
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| verifiedrevid = 464374712 |
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| Name = Prenol |
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| Name = Prenol |
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| ImageFile1 = prenol structure.png |
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| ImageFile1 = Prenol structure.png |
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| ImageSize1 = 160px |
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| ImageSize1 = 160px |
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| ImageName1 = Skeletal formula of prenol |
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| ImageName1 = Skeletal formula of prenol |
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| ImageFile2 = Prenol-3D-balls.png |
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| ImageFile2 = Prenol-3D-balls.png |
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| ImageSize2 = 180px |
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| ImageSize2 = 180px |
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| ImageName2 = Ball-and-stick model |
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| ImageName2 = Ball-and-stick model |
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| IUPACName = 3-Methyl-2-buten-1-ol |
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| PIN = 3-Methylbut-2-en-1-ol |
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| OtherNames= 3,3-Dimethylallyl alcohol |
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| OtherNames = 3,3-Dimethylallyl alcohol |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| InChI = 1/C5H10O/c1-5(2)3-4-6/h3,6H,4H2,1-2H3 |
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| InChI = 1/C5H10O/c1-5(2)3-4-6/h3,6H,4H2,1-2H3 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C5H10O/c1-5(2)3-4-6/h3,6H,4H2,1-2H3 |
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| StdInChI = 1S/C5H10O/c1-5(2)3-4-6/h3,6H,4H2,1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = ASUAYTHWZCLXAN-UHFFFAOYSA-N |
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| StdInChIKey = ASUAYTHWZCLXAN-UHFFFAOYSA-N |
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| CASNo = 556-82-1 |
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| CASNo = 556-82-1 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| EC-number = 209-141-4 |
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| EC_number = 209-141-4 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10700 |
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| ChemSpiderID = 10700 |
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| PubChem = 11173 |
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| PubChem = 11173 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 55MY0HM445 |
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| UNII = 55MY0HM445 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| SMILES = OC\C=C(/C)C |
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| SMILES = OC\C=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 name="SIDS">{{SIDS-ref|id=556821|name=3-Methyl-2-buten-1-ol|date=May 2005}}.</ref> |
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| Properties_ref = <ref name="SIDS">{{SIDS-ref| id=556821 |name=3-Methyl-2-buten-1-ol|date=May 2005}}.</ref> |
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| Formula = C<sub>5</sub>H<sub>10</sub>O |
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| Formula = C<sub>5</sub>H<sub>10</sub>O |
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| MolarMass = 86.132 g/mol |
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| MolarMass = 86.132 g/mol |
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| Density = 0.848 g/cm<sup>3</sup> |
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| Density = 0.848 g/cm<sup>3</sup> |
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| MeltingPt = −59 °C (calculated) |
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| MeltingPtC = −59 |
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| MeltingPt_notes = (calculated) |
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| BoilingPt = approx. 142 °C |
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| BoilingPtC = 142 |
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| Solubility = 17 g/100 ml (20 ºC) |
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| BoilingPt_notes = (approximation) |
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| VaporPress = 3.17 hPa (25 ºC, extrapolated) |
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| Solubility = 17 g/100 ml (20 °C) |
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| LogP = 0.91 |
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| VaporPressure = 3.17 hPa (25 °C, extrapolated) |
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}} |
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| LogP = 0.91 |
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| Section7 = {{Chembox Hazards |
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| Reference = <ref name="SIDS"/><ref>{{citation | title = HSNO Chemical Classification Information Database | url = http://www.ermanz.govt.nz/Chemicals/ChemicalDisplay.aspx?SubstanceID=13093 | publisher = New Zealand Environmental Risk Management Agency | accessdate = 2009-08-31}}.</ref> |
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| EUIndex = not listed |
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| GHSPictograms = {{GHS flame|Flam. Liq. 3}}{{GHS exclamation mark|Acte Tox. (oral) 4}} |
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| GHSSignalWord = WARNING |
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| HPhrases = {{H-phrases|226|302}} |
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| PPhrases = {{P-phrases|210|233|240|241|242|243|264|270 |301+312|303+361+353|330|370+378 |403+235|501}} |
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| FlashPt = 43.3 ºC (110 ºF)<ref group="note">BASF gives a value for the flash point of prenol of 51.5 ºC (125 ºF), which is used in the OECD Screening Information Data Set (SIDS): the difference in the two values does not alter the safety classification of prenol as a category 3 flammable liquid (]) or class II combustible liquid (U.S., 29 C.F.R § 1910.106, ]).</ref> |
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}} |
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}} |
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|Section7={{Chembox Hazards |
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| Hazards_ref = <ref name="SIDS"/><ref>{{citation | title = HSNO Chemical Classification Information Database | url = http://www.ermanz.govt.nz/Chemicals/ChemicalDisplay.aspx?SubstanceID=13093 | publisher = New Zealand Environmental Risk Management Agency | accessdate = 2009-08-31 }}{{dead link|date=March 2018 |bot=InternetArchiveBot |fix-attempted=yes }}.</ref> |
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| GHSPictograms = {{GHS flame|Flam. Liq. 3}}{{GHS exclamation mark|Acte Tox. (oral) 4}} |
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| GHSSignalWord = WARNING |
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| HPhrases = {{H-phrases|226|302}} |
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| PPhrases = {{P-phrases|210|233|240|241|242|243|264|270 |301+312|303+361+353|330|370+378 |403+235|501}} |
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| FlashPtC = 43.3 |
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| FlashPt_ref = <ref group="note">BASF gives a value for the flash point of prenol of 51.5 °C (125 °F), which is used in the OECD Screening Information Data Set (SIDS): the difference in the two values does not alter the safety classification of prenol as a category 3 flammable liquid (]) or class II combustible liquid (U.S., 29 C.F.R § 1910.106, ]).</ref> |
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}} |
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}} |
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'''Prenol''', or '''3-methyl-2-buten-1-ol''', is a natural ]. It is one of the most simple ]s. It is a clear colorless oil that is reasonably soluble in water and miscible with most common organic solvents. It has a fruity odor and is used occasionally in perfumery. |
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Prenol occurs naturally in citrus fruits, cranberry, bilberry, currants, grapes, raspberry, blackberry, tomato, white bread, hop oil, coffee, arctic bramble, cloudberry and passion |
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fruit.<ref name="SIDS"/> It is also manufactured industrially by ] (in ], ]) and by ] (in Asia) as an intermediate to pharmaceuticals and aroma compounds. Global production in 2001 was between 6000 and 13,000 tons.<ref name="SIDS"/> |
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==Industrial production== |
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Prenol is produced industrially by the reaction of ] with ], followed by the isomerization of the resulting ] (3-methyl-3-buten-1-ol).<ref name="SIDS"/><ref>See, e.g., {{citation | first1 = S. B. | last1 = Kogan | first2 = M. | last2 = Kaliya | first3 = N. | last3 = Froumin | title = Liquid phase isomerization of isoprenol into prenol in hydrogen environment | journal = Appl. Catal. A: Gen. | volume = 297 | issue = 2 | year = 2006 | pages = 231–36 | doi = 10.1016/j.apcata.2005.09.010}}.</ref> |
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:] |
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{{clear|left}} |
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==Uses== |
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Prenol is mainly used as a precursor to ], an intermediate in the industrial production of ], E, and K. For this purpose, prenol is oxidized to the aldehyde ].<ref name=KO>{{cite book |doi=10.1002/0471238961.2005181602120504.a01.pub2|chapter=Terpenoids |title=Kirk-Othmer Encyclopedia of Chemical Technology |year=2006 |last1=Sell |first1=Charles S. |isbn=0471238961 }}</ref> |
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===Polyprenols=== |
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{{main|Polyprenol}} |
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Prenol is a building block of isoprenoid alcohols, which have the general formula: |
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:H–<sub>''n''</sub>–OH |
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The repeating C<sub>5</sub>H<sub>8</sub> ] in the brackets is called ], and these compounds are sometimes called 'isoprenols'.<ref>See, e.g., {{citation | first1 = Robert D. | last1 = Goodfellow | first2 = Yung-Sheng | last2 = Huang | first3 = Harold E. Jr. | last3 = Radtke | title = Isoprenol biosynthesis in the fly, ''Sarcophaga bullata'' | journal = Insect Biochem. | volume = 2 | issue = 8 | year = 1972 | pages = 467–75 | doi = 10.1016/0020-1790(72)90027-3}}.</ref> They should not be confused with ], which is an isomer of prenol with a terminal double bond. The simplest isoprenoid alcohol is ] (''n'' = 2): higher oligomers include ] (''n'' = 3) and ] (''n'' = 4). |
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When the isoprene unit attached to the alcohol is ], the ] is referred to as a ]. Dolichols are important as glycosyl carriers in the ] of ]. They also play a major role in protecting cellular membranes, stabilising cell proteins and supporting the body's immune system. |
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Prenol is polymerized by ]s; when there are at least five isoprene units (''n'' in the above formula is greater than or equal to five), the ] is called a ]. Polyprenols can contain up to 100 isoprene units (''n'' = 100) linked end to end with the ] (–OH) remaining at the end. These long-chain isoprenoid alcohols are also called ‘terpenols’. They are important in the acylation of ], ]s, and fat-soluble ], ] and ]. |
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Polyprenols also play a vital role in ]. Research indicates that ingested polyprenols are metabolised by human and animal liver into ]s which then take part in the ] and are therefore easily assimilated by humans and animals. The pharmacological activity of polyprenols is based on their substitutive effect in the case of dolichol deficits which are observed with chronic inflammatory, degenerative and oncological diseases.<ref>{{citation | last1 = Edlund | first1 = C. | last2 = Söderberg | first2 = M. | last3 = Kristensson | first3 = K. | title = Isoprenoids in aging and neurodegeneration | journal = Neurochem. Int. | year = 1994 | volume = 25 | issue = 1 | pages = 35–38 | doi = 10.1016/0197-0186(94)90050-7 | pmid = 7950967}}.</ref> |
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Live conifer needles are one of the richest and most widely available sources for polyprenol extraction in the world. Commercial extraction of polyprenols involves a soft extraction procedure that enables them to be extracted without destroying their biological activity.<ref>{{citation | title = Company Announcement – Report on Opening of Tomsk Production Facility | url = http://www.asx.com.au/asx/statistics/displayAnnouncement.do?display=pdf&idsId=00826503 | publisher = Solagran Ltd. | date = 2008-03-27 | accessdate = 2009-08-31}}.</ref> |
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==Notes== |
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{{reflist|group="note"}} |
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==References== |
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{{reflist}} |
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==External links== |
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*{{SIDS| id=556821 |name=3-Methyl-2-buten-1-ol}} |
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] |
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] |
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] |