{{Chembox | Name = Amyrins | ImageFile = alpha-amyrin.svg | ImageCaption = α-Amyrin | ImageFile1 = beta-amyrin.svg | ImageCaption1 = β-Amyrin | IUPACName = α: (3β)-Urs-12-en-3-ol<br />β: (3β)-Olean-12-en-3-ol<br />δ: (3β)-Olean-13(18)-en-3-ol | OtherNames = α: α-Amyrenol; α-Amirin; α-Amyrine; Urs-12-en-3β-ol; Viminalol<br />β: β-Amyrenol; β-Amirin; β-Amyrine; Olean-12-en-3β-ol; 3β-Hydroxyolean-12-ene |Section1={{Chembox Identifiers | CASNo = 638-95-9 | CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Comment = (α) | CASNo1 = 559-70-6 | CASNo1_Ref = {{cascite|correct|CAS}} | CASNo1_Comment = (β) | CASNo2 = 508-04-3 | CASNo2_Ref = {{cascite|correct|CAS}} | CASNo2_Comment = (δ) | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 30ZAG40J8N | UNII_Comment = (α) | UNII1_Ref = {{fdacite|correct|FDA}} | UNII1 = KM8353IPSO | UNII1_Comment = (β) | PubChem = 73170 | PubChem_Comment = (α) | PubChem1 = 73145 | PubChem1_Comment = (β) | PubChem2 = 12358447 | PubChem2_Comment = (δ) | ChemSpiderID = 65935 | ChemSpiderID_Comment = (α) | ChemSpiderID1 = 65921 | ChemSpiderID1_Comment = (β) | ChemSpiderID2 = 26333109 | ChemSpiderID2_Comment = (δ) | SMILES = O[C@H]2CC[C@@]1([C@@H]3[C@](CC[C@H]1C2(C)C)(C)[C@]5(C(=C/C3)\[C@@H]4[C@@H](C)[C@H](C)CC[C@]4(C)CC5)C)C | SMILES_Comment = (α) | StdInChI = 1S/C30H50O/c1-19-11-14-27(5)17-18-29(7)21(25(27)20(19)2)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h9,19-20,22-25,31H,10-18H2,1-8H3/t19-,20+,22+,23-,24+,25+,27-,28+,29-,30-/m1/s1 | StdInChI_Comment = (α) | StdInChIKey = FSLPMRQHCOLESF-SFMCKYFRSA-N | SMILES1 = C[C@@]12CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)[C@@H]1CC(CC2)(C)C)C | SMILES1_Comment = (β)
| InChI3 = 1S/C30H50O/c1-25(2)15-16-27(5)17-18-29(7)20(21(27)19-25)9-10-23-28(6)13-12-24(31)26(3,4)22(28)11-14-30(23,29)8/h9,21-24,31H,10-19H2,1-8H3/t21-,22-,23+,24-,27+,28-,29+,30+/m0/s1 | InChI3_Comment = (β) | InChIKey3 = JFSHUTJDVKUMTJ-QHPUVITPSA-N }} |Section2={{Chembox Properties | C=30 | H=50 | O=1 | Appearance = | Density = | MeltingPt = α: 186 °C<ref>''Merck Index'', 11th Edition, '''653'''</ref><br />β: 197-187.5 °C<ref>''Merck Index'', 11th Edition, '''654'''</ref> | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}
The '''amyrins''' are three closely related natural chemical compounds of the triterpene class. They are designated α-amyrin (ursane skeleton),<ref>{{cite journal | pmid = 17473469 | volume=55 | issue=5 | title=Production of triterpene acids by cell suspension cultures of Olea europaea | journal=Chemical and Pharmaceutical Bulletin | pages=784–8 | last1 = Saimaru | first1 = H | last2 = Orihara | first2 = Y | last3 = Tansakul | first3 = P | last4 = Kang | first4 = YH | last5 = Shibuya | first5 = M | last6 = Ebizuka | first6 = Y | doi=10.1248/cpb.55.784| year=2007 | doi-access = free }}</ref> '''β-amyrin''' (oleanane skeleton),<ref>{{cite journal | pmid = 16962103 | doi=10.1016/j.febslet.2006.08.044 | volume=580 | issue=22 | title=Dammarenediol-II synthase, the first dedicated enzyme for ginsenoside biosynthesis, in Panax ginseng | journal=FEBS Letters | pages=5143–9 | last1 = Tansakul | first1 = P | last2 = Shibuya | first2 = M | last3 = Kushiro | first3 = T | last4 = Ebizuka | first4 = Y| year=2006 | s2cid=20731479 | doi-access = free }}</ref> and δ-amyrin. Each is a pentacyclic triterpenol with the chemical formula C<sub>30</sub>H<sub>50</sub>O. They are widely distributed in nature and have been isolated from a variety of plant sources such as epicuticular wax. In plant biosynthesis, α-amyrin is the precursor of ursolic acid and β-amyrin is the precursor of oleanolic acid.<ref>{{cite journal |last1=Babalola |first1=Ibrahim T |last2=Shode |first2=Francis O |title=Ubiquitous Ursolic Acid: A Potential Pentacyclic Triterpene Natural Product |journal=Journal of Pharmacognosy and Phytochemistry |date=2013 |volume=2 |issue=2 |pages=214–222 |url=https://www.phytojournal.com/vol2Issue2/Issue_july_2013/37.1.pdf |access-date=31 October 2022 |language=en |issn=2278-4136}}</ref> All three amyrins occur in the surface wax of tomato fruit.<ref>{{cite journal|pmc=5278499 | pmid=28194155 | doi=10.3389/fpls.2017.00021 | volume=8 | title=Functional Characterization of CYP716 Family P450 Enzymes in Triterpenoid Biosynthesis in Tomato | journal=Frontiers in Plant Science | page=21 | last1 = Yasumoto | first1 = S | last2 = Seki | first2 = H | last3 = Shimizu | first3 = Y | last4 = Fukushima | first4 = EO | last5 = Muranaka | first5 = T| year=2017 | doi-access=free }}</ref><ref name=Bauer>{{cite journal |journal=European Food Research and Technology |date=2004 |volume=219 |pages=487–491 |first1=Stefan |last1=Bauer |first2=Erhard |last2=Schulte | first3=Hans-Peter |last3=Thier | title=Composition of the surface wax from tomatoes II. Quantification of the components at the ripe red stage and during ripening |doi=10.1007/s00217-004-0944-z|s2cid=90472894 }}</ref> α-Amyrin is found in dandelion coffee.{{citation needed|date=November 2016}}
A study demonstrated that α,β-amyrin exhibits long-lasting antinociceptive and anti-inflammatory properties in 2 models of persistent nociception via activation of the cannabinoid receptors CB1 and CB2 and by inhibiting the production of cytokines and expression of NF-κB, CREB, and cyclooxygenase 2.<ref>{{Cite journal|last1=Simão da Silva|first1=Kathryn A.B.|last2=Paszcuk|first2=Ana F.|last3=Passos|first3=Giselle F.|last4=Silva|first4=Eduardo S.|last5=Bento|first5=Allisson Freire|last6=Meotti|first6=Flavia C.|last7=Calixto|first7=João B.|date=August 2011|title=Activation of cannabinoid receptors by the pentacyclic triterpene α,β-amyrin inhibits inflammatory and neuropathic persistent pain in mice|journal=Pain|language=ENGLISH|volume=152|issue=8|pages=1872–1887|doi=10.1016/j.pain.2011.04.005|pmid=21620566|s2cid=23484784|issn=0304-3959}}</ref>
== References == {{reflist}}
Category:Secondary alcohols Category:Triterpenes