Amyrin

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Amyrins
Alpha-amyrin.svg
α-Amyrin
Beta-amyrin.svg
β-Amyrin
Names
IUPAC names
α: (3β)-Urs-12-en-3-ol
β: (3β)-Olean-12-en-3-ol
δ: (3β)-Olean-13(18)-en-3-ol
Other names
α: α-Amyrenol; α-Amirin; α-Amyrine; Urs-12-en-3β-ol; Viminalol
β: β-Amyrenol; β-Amirin; β-Amyrine; Olean-12-en-3β-ol; 3β-Hydroxyolean-12-ene
Identifiers
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.010.321
Properties
C30H50O
Molar mass 426.73 g·mol−1
Melting point α: 186 °C[1]
β: 197-187.5 °C[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

The amyrins are three closely related natural chemical compounds of the triterpene class. They are designated α-amyrin (ursane skeleton),[3] β-amyrin (oleanane skeleton) [4] and δ-amyrin. Each is a pentacyclic triterpenol with the chemical formula C30H50O. 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.[5] All three amyrins occur in the surface wax of tomato fruit.[6][7] α-Amyrin is found in dandelion coffee.[citation needed]

References[edit]

  1. ^ Merck Index, 11th Edition, 653
  2. ^ Merck Index, 11th Edition, 654
  3. ^ Saimaru, H; Orihara, Y; Tansakul, P; Kang, YH; Shibuya, M; Ebizuka, Y. "Production of triterpene acids by cell suspension cultures of Olea europaea". Chem Pharm Bull (Tokyo). 55: 784–8. PMID 17473469. 
  4. ^ Tansakul, P; Shibuya, M; Kushiro, T; Ebizuka, Y. "Dammarenediol-II synthase, the first dedicated enzyme for ginsenoside biosynthesis, in Panax ginseng". FEBS Lett. 580: 5143–9. doi:10.1016/j.febslet.2006.08.044. PMID 16962103. 
  5. ^ http://www.phytojournal.com/vol2Issue2/Issue_july_2013/37.1.pdf
  6. ^ https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5278499
  7. ^ Bauer, Stefan; Schulte, Erhard; Thier, Hans-Peter (2004). "Composition of the surface wax from tomatoes II. Quantification of the components at the ripe red stage and during ripening". European Food Research and Technology. 219: 487–491. doi:10.1007/s00217-004-0944-z.