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Latest revision as of 12:25, 21 October 2021 edit undoLeschnei (talk | contribs)Extended confirmed users, Pending changes reviewers85,483 editsm Disambiguate Silphium to Silphium (antiquity) using popups |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 407484618 |
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| verifiedrevid = 443390598 |
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| Name = Angelic acid |
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| Name = Angelic acid |
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| ImageFile = Angelic acid.png |
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| ImageFile = Angelic acid.png |
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| ImageSize1 = 145px |
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| ImageSize1 = 145px |
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| ImageName1 = Ball-and-stick model of angelic acid |
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| ImageName1 = Ball-and-stick model of angelic acid |
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| IUPACName = (''Z'')-2-methylbut-2-enoic acid |
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| PIN = (2''Z'')-2-Methylbut-2-enoic acid |
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| OtherNames = |
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| OtherNames = (''Z'')-2-Methylbut-2-enoic acid |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| StdInChIKey = UIERETOOQGIECD-ARJAWSKDSA-N |
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| StdInChIKey = UIERETOOQGIECD-ARJAWSKDSA-N |
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| SMILES1 = O=C(O)\C(=C/C)C |
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| SMILES1 = O=C(O)\C(=C/C)C |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 565-63-9 |
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| CASNo = 565-63-9 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 54U4ZPB36F |
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| PubChem = 643915 |
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| PubChem = 643915 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 36431 |
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| ChEBI = 36431 |
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| SMILES = C/C=C(C)\C(O)=O |
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| SMILES = C/C=C(C)\C(O)=O |
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'''Angelic acid''' is a ] ] ]. It is mostly found in the plants of the family ]. German pharmacist ] isolated angelic acid in 1842 from the roots of garden angelica ('']'') which gave the acid its name. Angelic acid is a volatile solid with a biting taste and pungent sour odor. It is the '']'' ] of 2-methyl-2-butenoic acid, which easily converts to the ''cis'' isomer, ], upon heating or reaction with inorganic acids. The reverse transformation occurs much less readily. The salts and esters of angelic acid are called '''angelates'''. Angelic acid ]s are the active components of herbal medicine used against a wide range of various health disturbances including pains, fever, ], heartburn, etc. |
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'''Angelic acid''' is a ] ] ], mostly found in the plants of the family ]. It is a volatile solid with a biting taste and pungent sour odor. It is the '']'' ] of 2-methyl-2-butenoic acid, which easily converts to the ''trans'' isomer, ], upon heating or reaction with inorganic acids. The reverse transformation occurs much less readily. The salts and esters of angelic acid are called '''angelates'''. Angelic acid ]s are the active components of herbal medicine used against a wide range of various health disturbances including pains, fever, ], heartburn, etc. |
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==Name and discovery== |
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==Name and discovery== |
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Angelic acid was first isolated by the German pharmacist Ludwig Andreas Buchner (1813–1897) in 1842 from the roots of the garden plant angelica ('']'') that gave the acid its name.<ref>{{cite journal|author = Buchner, L. A.|year = 1842|title = Ueber eine eigenthümliche flüchtige Säure aus der Angelicawurzel: Eine briefliche Mittheilung|journal = Justus Liebigs Ann. Chem.|volume = 42|pages = 226–233|doi = 10.1002/jlac.18420420211}}</ref> |
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Angelic acid was first isolated by the German pharmacist Ludwig Andreas Buchner (1813–1897) in 1842 from the roots of the garden plant angelica ('']''), which gave the acid its name.<ref>{{cite journal|author = Buchner, L. A.|year = 1842|title = Ueber eine eigenthümliche flüchtige Säure aus der Angelicawurzel: Eine briefliche Mittheilung|journal = Justus Liebigs Ann. Chem.|volume = 42|issue = 2|pages = 226–233|doi = 10.1002/jlac.18420420211|url = https://zenodo.org/record/1426967}}</ref> |
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==Occurrence== |
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==Occurrence== |
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Angelic acid occurs in the roots of many plants, especially of the family ]. These plants include ''Angelica archangelica'', ''Peucedanum ostruthium'' (]), ''Levisticum officinale'' (]),<ref name=b2/><ref>K. V. Peter , Woodhead Publishing, 2004, ISBN 1855737213 p. 96</ref> ''Euryangium Sumbul'' and '']''. In the latter plant, it is present in the resin called ], and the oil of carrot also contains angelic acid.<ref name=carrot>{{cite journal|last1=Sonobe|first1=Hiromi|last2=Kamps|first2=Laverne R.|last3=Mazzola|first3=Eugene P.|last4=Roach|first4=John A. G.|title=Isolation and identification of a new conjugated carbofuran metabolite in carrots: angelic acid ester of 3-hydroxycarbofuran|journal=Journal of Agricultural and Food Chemistry|volume=29|issue=6|pages=1125|year=1981|pmid=7320331|doi=10.1021/jf00108a006}}</ref> Sumbul plants might contain not angelic acid itself, but a larger complex which breaks into angelic acid upon processing.<ref>J. O. Braithwaite , J. & A. Churchill, 1887, p. 14</ref> The acid can also be extracted from the oil of ] flowers, and 85% of Roman chamomile ('']'') oil consists of esters of angelic and tiglic acids;<ref name=b3>Ernest Small , National Research Council Canada, 2006, ISBN 0660190737 p. 288</ref><ref>Lyle E. Craker, James E. Simon , Routledge, 1986, ISBN 1560220430 p. 257</ref> it also contains isobutyl angelate and amyl angelate.<ref>], ], ] , Longmans, Green, 1888, p. 266</ref> The acid content is highest in ''Angelica archangelica''<ref name=b1>William Allen Miller, Herbert McLeod , Vol. 3: Chemical physics, p. 958</ref> where it is about 0.3%.<ref name=b2>Rudolf Fritz Weiss , Thieme, 2001, ISBN 158890069X pp. 46, 91, 236</ref> |
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Angelic acid occurs in the roots of many plants, especially of the family ]. These plants include '']'', '']'' (masterwort), '']'' (lovage),<ref name=b2/><ref>K. V. Peter , Woodhead Publishing, 2004, {{ISBN|1-85573-721-3}} p. 96</ref> '']'' and '']''. In the latter plant, it is present in the resin called ], and the oil of carrot also contains angelic acid.<ref name=carrot>{{cite journal|last1=Sonobe|first1=Hiromi|last2=Kamps|first2=Laverne R.|last3=Mazzola|first3=Eugene P.|last4=Roach|first4=John A. G.|title=Isolation and identification of a new conjugated carbofuran metabolite in carrots: angelic acid ester of 3-hydroxycarbofuran|journal=Journal of Agricultural and Food Chemistry|volume=29|issue=6|pages=1125–9|year=1981|pmid=7320331|doi=10.1021/jf00108a006}}</ref> Sumbul plants might contain not angelic acid itself, but a larger complex which breaks into angelic acid upon processing.<ref>J. O. Braithwaite , J. & A. Churchill, 1887, p. 14</ref> The acid can also be extracted from the oil of ] flowers, and 85% of Roman chamomile ('']'') oil consists of esters of angelic and tiglic acids;<ref name=b3>Ernest Small , National Research Council Canada, 2006, {{ISBN|0-660-19073-7}} p. 288</ref><ref>Lyle E. Craker, James E. Simon , Routledge, 1986, {{ISBN|1-56022-043-0}} p. 257</ref> it also contains isobutyl angelate and amyl angelate.<ref>], ], ] , Longmans, Green, 1888, p. 266</ref> The acid content is highest in ''Angelica archangelica''<ref name=b1>William Allen Miller, Herbert McLeod , Vol. 3: Chemical physics, p. 958</ref> where it is about 0.3%.<ref name=b2>Rudolf Fritz Weiss , Thieme, 2001, {{ISBN|1-58890-069-X}} pp. 46, 91, 236</ref> |
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==Properties== |
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==Properties== |
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Angelic acid is a volatile solid with a biting taste and pungent sour odor. It crystallizes in colorless monoclinic prisms which dissolve rapidly in ]<ref>Friedrich Wöhler , p. 124</ref> or hot water and slowly in cold water. Angelic and ] are '']'' and cis isomers of 2-methyl-2-butenoic acid, respectively. The former can be entirely converted to the latter by boiling for about 40 hours, by reaction with ] and other acids,<ref name=b1/> by heating with a base to a temperature above 100 °C,<ref name=carrot/> or simply by storing the acid for about 25 years.<ref>, p. 92</ref> The reverse transformation occurs much less readily; it can be induced by ultraviolet light, but not with visible light. The conversion rate is low and only 0.36 g of angelic acid could be obtained from 13 g of tiglic acid after 43-day irradiation with a 500-watt lamp. Despite being the trans isomer, angelic acid has a lower melting point and higher acid dissociation constant than tiglic acid,<ref>{{cite journal|doi=10.1021/ja01144a518|last1=Pelletier|first1=S. W.|year=1952|pages=6292|volume=74|journal=Journal of the American Chemical Society|last2=McLeish|first2=William L.|title=The Ultraviolet-induced Isomerization of Tiglic Acid to Angelic Acid}}</ref> although the opposite trends are usually observed.<ref>Vickie Vaclavik, Vickie A. Vaclavik, Elizabeth W. Christian , Springer, 2007, ISBN 0387699392, p. 282</ref><ref> D. Nasipuri , New Age International, 1994, ISBN 8122405703, p. 192</ref> |
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Angelic acid is a volatile solid with a biting taste and pungent sour odor. It crystallizes in colorless monoclinic prisms which dissolve rapidly in ]<ref>Friedrich Wöhler , p. 124</ref> or hot water and slowly in cold water. Angelic and ] are '']'' and ''trans'' isomers of 2-methyl-2-butenoic acid, respectively. The former can be entirely converted to the latter by boiling for about 40 hours, by reaction with ] and other acids,<ref name=b1/> by heating with a base to a temperature above 100 °C,<ref name=carrot/> or simply by storing the acid for about 25 years.<ref>, p. 92</ref> The reverse transformation occurs much less readily; it can be induced by ultraviolet light, but not with visible light. The conversion rate is low and only 0.36 g of angelic acid could be obtained from 13 g of tiglic acid after 43-day irradiation with a 500-watt lamp. Being the ''cis'' isomer, angelic acid has a lower melting point and higher acid dissociation constant than tiglic acid,<ref>{{cite journal|doi=10.1021/ja01144a518|last1=Pelletier|first1=S. W.|year=1952|pages=6292–6293|volume=74|issue=24|journal=Journal of the American Chemical Society|last2=McLeish|first2=William L.|title=The Ultraviolet-induced Isomerization of Tiglic Acid to Angelic Acid}}</ref> in accordance to usually observed trends.<ref>Vickie Vaclavik, Vickie A. Vaclavik, Elizabeth W. Christian , Springer, 2007, {{ISBN|0-387-69939-2}}, p. 282</ref><ref> D. Nasipuri , New Age International, 1994, {{ISBN|81-224-0570-3}}, p. 192</ref> |
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Angelic acid reacts with ] and bromine producing ] and dibromovaleric acids, respectively, with a yield of 60–70%. Chlorovaleric and iodovaleric acids are obtained using ] and ]s, respectively. The salts of angelic acid are called angelates. Angelates of ]s ''M'' have a general formula M(C<sub>5</sub>H<sub>7</sub>O<sub>2</sub>)<sub>2</sub> and form white, water-soluble crystals.<ref name=b1/> |
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Angelic acid reacts with ] and bromine producing ] and dibromovaleric acids, respectively, with a yield of 60–70%. Chlorovaleric and iodovaleric acids are obtained using ] and ]s, respectively. The salts of angelic acid are called angelates. Angelates of ]s ''M'' have a general formula M(C<sub>5</sub>H<sub>7</sub>O<sub>2</sub>)<sub>2</sub> and form white, water-soluble crystals.<ref name=b1/> |
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==Applications== |
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==Applications== |
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