(R,R)-chrysanthemol

Base Information

• Chemical Name: (R,R)-chrysanthemol
• CAS No.: 32989-74-5
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.252
• UNII: JU6FV4QD33
• Nikkaji Number: J408.368G
• Wikidata: Q74417774
• Mol file: 32989-74-5.mol

Synonyms:(R,R)-chrysanthemol;(1R,3R)-Chrysanthemol;JU6FV4QD33;Chrysanthemol, (1R,3R)-;1R,3R-Chrysanthemyl alcohol;trans-(+)-Chrysanthemyl alcohol;UNII-JU6FV4QD33;Cyclopropanemethanol, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-, (1R,3R)-;Cyclopropanemethanol, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (1R-trans)-;32989-74-5;trans-Chrysanthemyl alcohol;SCHEMBL10992837;CHEBI:143898;[(1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl]methanol;(1R)-2,2-Dimethyl-3alpha-(2-methyl-1-propenyl)cyclopropane-1beta-methanol;(1r,3r)-trans-(2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl)methanol;[(1R,3R)-2,2-DIMETHYL-3-(2-METHYLPROP-1-EN-1-YL)CYCLOPROPYL]METHANOL

Chemical Property of (R,R)-chrysanthemol

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 175

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CC1C(C1(C)C)CO)C
• Isomeric SMILES: CC(=C[C@@H]1[C@H](C1(C)C)CO)C

Technology Process of (R,R)-chrysanthemol

There total 14 articles about (R,R)-chrysanthemol 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:

dimethylallyl diphosphate (358-72-5) + isopentyl pyrophosphate (358-71-4) → Nerol (106-25-2) + Geraniol (106-24-1) + (R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol (498-16-8,21090-68-6) + (2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol (3790-71-4) + Farnesol (106-28-5) + γ-geraniol (13066-51-8) + (1R,3R)-Chrysanthemol (32989-74-5)

Guidance literature:

dimethylallyl diphosphate; isopentyl pyrophosphate; With farnesyl diphosphate synthase from Artemisia tridentata ssp. Spiciformis; In aq. buffer; at 30 ℃; for 2h; pH=7.6; Enzymatic reaction;

With calf intestinal phosphatase; In aq. buffer; at 37 ℃; for 1h; Enzymatic reaction;

DOI:10.1021/jacs.7b07608

Reference yield:

trans-chrysanthemic acid (827-90-7,2259-14-5,2935-23-1,4638-92-0,10453-89-1,15259-78-6,26771-06-2,26771-11-9,705-16-8) → trans-chrysanthemyl alcohol (2861-25-8,2861-26-9,5617-92-5,18383-58-9,18383-59-0,32989-74-5,52153-04-5,76704-87-5,78780-10-6)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether;

DOI:10.1039/P19720000642

Reference yield:

chrysanthemumic acid methyl ester (5460-63-9) → trans-chrysanthemyl alcohol (2861-25-8,2861-26-9,5617-92-5,18383-58-9,18383-59-0,32989-74-5,52153-04-5,76704-87-5,78780-10-6) + cis-chrysanthemyl alcohol (2861-25-8,2861-26-9,5617-92-5,18383-58-9,18383-59-0,32989-74-5,52153-04-5,76704-87-5,78780-10-6)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 3h; Yield given. Yields of byproduct given; Heating;

upstream raw materials:

dimethylallyl diphosphate

isopentyl pyrophosphate

methyl (dl)-trans-chrysanthemate

trans-chrysanthemic acid

Downstream raw materials:

C₁₇H₂₄N₂O₂S

cis-chrysanthemyl acetate

2,5,5-Trimethyl-heptan

6-(1,1-dimethyl-allyl)-4-methyl-2-phenyl-3,6-dihydro-2H-[1,2]oxazine

Refernces

• 1、 Thulasiram, Hirekodathakallu V.,Erickson, Hans K.,Poulter, C. Dale. "A common mechanism for branching, cyclopropanation, and cyclobutanation reactions in the isoprenoid biosynthetic pathway". . p. 1966 - 1971. Retrieved 2008/09/18.
• 2、 Crammer, Bernard,Goldschmidt, Zeev,Ikan, Raphael,Cohen, Shmuel. "Studies of Chrysanthemic Acid Derivatives: Catalyses Reactions of 3-(2-Hydroxymethyl-3,3-dimethylcyclopropyl)-2-methylpropanol and Formation of a Novel Eight-membered Cyclic Sulphite". . p. 887 - 891. Retrieved 2007/10/02.