(2E,6R)-6-Hydroxy-2,6-dimethyl-2,7-octadienoic acid

Base Information

• Chemical Name: (2E,6R)-6-Hydroxy-2,6-dimethyl-2,7-octadienoic acid
• CAS No.: 83945-54-4
• Molecular Formula: C₁₀H₁₆O₃
• Molecular Weight: 184.235
• UNII: L4GCE5Q2XP
• Nikkaji Number: J807.003B,J2.496.615A
• Mol file: 83945-54-4.mol

Synonyms:(R)-Menthiafolic acid;L4GCE5Q2XP;Menthiafolic acid, (R)-;(E)-Linalool-1-oic acid;UNII-L4GCE5Q2XP;(2E,6R)-6-Hydroxy-2,6-dimethyl-2,7-octadienoic acid;2,7-Octadienoic acid, 6-hydroxy-2,6-dimethyl-, (2E,6R)-;2,7-Octadienoic acid, 6-hydroxy-2,6-dimethyl-, (R-(E))-;83945-54-4;(6R)-Menthiafolic acid

Chemical Property of (2E,6R)-6-Hydroxy-2,6-dimethyl-2,7-octadienoic acid

Chemical Property:

• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 184.109944368
• Heavy Atom Count: 13
• Complexity: 230

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CCCC(C)(C=C)O)C(=O)O
• Isomeric SMILES: C/C(=C\CC[C@](C)(C=C)O)/C(=O)O

Technology Process of (2E,6R)-6-Hydroxy-2,6-dimethyl-2,7-octadienoic acid

There total 8 articles about (2E,6R)-6-Hydroxy-2,6-dimethyl-2,7-octadienoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

9-(6-O-[(2E,6S)-2,6-dimethyl-6-hydroxy-2,7-octadienoyl]-β-D-glucopyranosyloxy)guaiacylglycerol (1370004-83-3) → guaiacyl glycerol (7095-33-2,27391-16-8,27431-21-6,38916-91-5,62078-66-4,84799-27-9,84822-99-1,1208-42-0) + (+)-2,6-dimethyl-6(S)-hydroxy-2-trans-2,7-octadecanoic acid (26187-81-5,28420-25-9,34935-27-8,67711-07-3,83945-54-4,98168-60-6,121843-29-6,124753-77-1,75979-26-9)

Guidance literature:

With water; sodium hydroxide;

DOI:10.1016/j.carres.2012.01.012

Reference yield:

phlebotrichin (83905-61-7) → (+)-2,6-dimethyl-6(S)-hydroxy-2-trans-2,7-octadecanoic acid (26187-81-5,28420-25-9,34935-27-8,67711-07-3,83945-54-4,98168-60-6,121843-29-6,124753-77-1,75979-26-9) + arbutin (497-76-7)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; water; at 90 ℃; for 4h;

DOI:10.1016/j.phytochem.2021.112782

Reference yield:

(E)-(R)-6-Hydroxy-2,6-dimethyl-octa-2,7-dienoic acid (2R,3R,4S,5R,6S)-3,4,5-triacetoxy-6-(4-acetoxy-phenoxy)-tetrahydro-pyran-2-ylmethyl ester → (6R)-2-trans-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid (83945-54-4) + arbutin (497-76-7)

Guidance literature:

With sodium hydroxide; In methanol; for 2h; Heating;

DOI:10.1016/0031-9422(82)80159-3

upstream raw materials:

gymnocladus saponin F₁

(6S)-2-trans-6-α-L-arabinopyranosyloxy-2,6-dimethyl-2,7-octadienoic acid

9-(6-O-[(2E,6S)-2,6-dimethyl-6-hydroxy-2,7-octadienoyl]-β-D-glucopyranosyloxy)guaiacylglycerol

9-(6-O-[(2E,6S)-2,6-dimethyl-6-hydroxy-2,7-octadienoyl]-β-D-glucopyranosyloxy)syringoylglycerol

Refernces

• 1、 Choi, Seong Yeon,Jang, Hyeon Seok,Jeong, Birang,Kim, Juyeol,Kwon, Yong Soo,Lee, Jiho,Park, Jinyoung,Yang, Heejung. "α-Glucosidic hydroquinone derivatives from Viburnum erosum". . . Retrieved 2021/05/03.
• 2、 Konoshima, Takao,Kozuka, Mutsuo,Kimura, Takeatsu. "Studies on the Constituents of Leguminous Plants. X. The Structures of New Triterpenoid Saponins from the Fruits of Gymnocladus chinensis BAILLON". . p. 1982 - 1990. Retrieved 2007/10/02.