EudesM-4(15)-ene-3α,11-diol

Base Information

• Chemical Name: EudesM-4(15)-ene-3α,11-diol
• CAS No.: 113773-90-3
• Molecular Formula: C₁₅H₂₆O₂
• Molecular Weight: 238.37
• Mol file: 113773-90-3.mol

Synonyms:(+)-Chrysanthemol;Chrysanthemol; Chrysanthemol (terpene); Eudesm-4(14)-en-3a,11-diol

Chemical Property of EudesM-4(15)-ene-3α,11-diol

Chemical Property:

• Refractive Index: 1.4699 (589.3 nm 25℃)
• Boiling Point: 91-92 °C(Press: 8 Torr)
• PKA: 14.98±0.60(Predicted)
• PSA: 40.46000
• Density: 1.03±0.1 g/cm3(Predicted)
• LogP: 2.89080

Purity/Quality:

99% ^*data from raw suppliers

Eudesm-4(15)-ene-3α,11-diol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of EudesM-4(15)-ene-3α,11-diol

There total 10 articles about EudesM-4(15)-ene-3α,11-diol 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: 91.8%

12-O-β-D-fucopyranosyl selin-4(15)-en-3β,11-diol 3-O-β-D-glucopyranoside → 3β-eudesm-4(14)-ene-3,11-diol (74799-32-9,113773-90-3)

Guidance literature:

With naringinase; acetate buffer; at 40 ℃; for 24h; pH=4.0;

DOI:10.1248/cpb.49.974

Reference yield: 50.0%

(+)-3α,4-epoxy-4β-eudesman-11-ol (200343-79-9) → (+)-chrysanthemol (113773-90-3)

Guidance literature:

With boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; In chloroform; at 0 ℃; for 0.166667h;

DOI:10.1246/cl.1997.1289

Reference yield:

eudesma-4,11-dien-3-one (473-08-5) → (+)-chrysanthemol (113773-90-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 86 percent / Li; liq. NH₃; NH₄Cl / diethyl ether / 0.42 h / -78 °C

2.1: 92 percent / LiAl(OtBu)3H / tetrahydrofuran / 18 h / 20 °C

3.1: N-chlorosuccinimide / tetrahydrofuran / 20 °C

3.2: 88 percent / PPh₃ / tetrahydrofuran / 3 h / 20 °C

4.1: 94 percent / m-CPBA / CH₂Cl₂ / 0.67 h / 20 °C

5.1: 92 percent / LiAlH₄ / diethyl ether / 10 h / 20 °C

6.1: 90 percent / LiBr; Li₂CO₃ / dimethylformamide / 5 h / 138 - 140 °C

7.1: 82 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 0.5 h / 0 °C

8.1: 50 percent / Bu₄NI; BF₃*Et₂O / CHCl₃ / 0.17 h / 0 °C

With N-chloro-succinimide; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; ammonia; tetra-(n-butyl)ammonium iodide; lithium; lithium carbonate; sodium hydrogencarbonate; ammonium chloride; lithium tri-t-butoxyaluminum hydride; 3-chloro-benzenecarboperoxoic acid; lithium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1002/jccs.200100042

upstream raw materials:

(+)-3α,4-epoxy-4β-eudesman-11-ol

eudesma-4,11-dien-3-one

r-eudesmol

(-)-dihydro-α-cyperol

Refernces

• 1、 Marukami,Kishi,Yoshikawa. "Medicinal flowers. IV. Marigold. (2): Structures of new ionone and sesquiterpene glycosides from Egyptian Calendula officinalis". . p. 974 - 978. Retrieved 2001.
• 2、 Fan, Cheng-Oi,Zhan, Zha-Jun,Li, Hui,Yue, Jian-Min. "Eudesmane-type sesquiterpene derivatives from Saussurea conica". . p. 1446 - 1451. Retrieved 2007/10/03.