Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17alpha)-

Base Information

• Chemical Name: Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17alpha)-
• CAS No.: 146-48-5
• Molecular Formula: C21H26N2O3
• Molecular Weight: 354.449
• Mol file: 146-48-5.mol

Synonyms:Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16.alpha.,17.alpha.)-;Methyl 17-hydroxyyohimban-16-carboxylate #;Yohimbol-16.alpha.-carboxylic acid, methyl ester;Benz[g]indolo[2,3-a]quinolizine, yohimban-16-carboxylic acid deriv.;SCHEMBL23244673;Yohimban-16.alpha.-carboxylic acid, 17.alpha.-hydroxy-, methyl ester;BLGXFZZNTVWLAY-MRXVMPTPSA-N;NCGC00485000-01;17alpha-hydroxy-yohimban-16alpha-carboxylic acid methyl ester

Chemical Property of Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17alpha)-

Chemical Property:

• Vapor Pressure: 1.27E-12mmHg at 25°C
• Melting Point: 231-233 °C(lit.)
• Refractive Index: 1.66
• Boiling Point: 543 °C at 760 mmHg
• PKA: 14.39±0.40(Predicted)
• Flash Point: 282.2 °C
• PSA: 65.56000
• Density: 1.31 g/cm³
• LogP: 2.58500
• Storage Temp.: Store at RT
• Solubility.: THF; DMSO; Chloroform
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 354.19434270
• Heavy Atom Count: 26
• Complexity: 555

Purity/Quality:

99% BY HPLC ^*data from raw suppliers

17α-Hydroxy-yohimban-16α-carboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25-39
• Safety Statements: 27-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O
• Isomeric SMILES: COC(=O)[C@H]1[C@H](CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O
• Description: Yohimbine is a natural alkaloid. It was first extracted from the barks of Corynanthe yohimbe, a species of Rubiaceae trees in West Africa. It was reported that, in the dried bark of Pausinystalia johimbe, the content of mixed alkaloids is higher than 6.1%, in which the main component is yohimbine, indicating a great prospect for development . Yohimbe bark has been used as an aphrodisiac in Africa since ancient times. In 1900, it was applied by Kowit and Muller to patients with impotence and paralytic insensitivity caused by neurasthenia and obtained curative effect. From then on, clinical application of yohimbine began. Currently, yohimbine is a pure plant preparation in the treatment of erectile dysfunction with more affirmation and more applications.
• Physical properties: Appearance: white powder. Solubility: soluble in ethanol, chloroform, and hot benzene; slightly soluble in water and ether, usually salified by hydrochloric acid to increase its solubility in water. Specific rotatory power (°): D22 +105° (in water). Melting point: 241–246?°C.
• Uses: Yohimbine occurs in Corinanthe johimbeK. and Rubiaceae trees. It is also foundin the roots of Rauwolfia serpentina L.and Apocyanaceae. Its derivatives areused therapeutically as adrenergic blockingagents. sexual dysfunction Obtained from leaves and bark of Corynanthe johimbe. Formerly used as an aphrodisiac in veterinary medicine, yohimbine works primarily by acting as an antagonist at α2-adrenergic receptors.
• Indications: This product is listed in the 2017 edition of the British Pharmacopoeia, 40 editions of the American Pharmacopoeia, and 9.0 edition of the European Pharmacopoeia. The main clinical application of yohimbine includes tablets and injections. It is mainly used to treat various types of impotence and sexual dysfunction in men.
• Clinical Use: Yohimbine increases heart rate and blood pressure as aresult of its blockade of 2-receptors in the CNS. It has beenused experimentally to treat male erectile impotence.

Technology Process of Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17alpha)-

There total 83 articles about Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17alpha)- 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: 100.0%

(1R,2S,4aR,13bS,14aS)-methyl-2-hydroxy-1,2,4a,5,7,8,13,13b,14,14a-decahydroindolo[2',3':3,4]pyrido-[1,2-b]isoquinoline-1-carboxylate (1011533-78-0) → Yohimbine (146-48-5)

Guidance literature:

With 10% Pd/C; hydrogen; In ethyl acetate; for 14h;

DOI:10.1021/ol702781q

Reference yield: 86.0%

(+)-yohimbinone (2671-57-0) → Yohimbine (146-48-5)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1021/ja00099a019

Reference yield:

(-)-Δ15,16-didehydroyohimbinone (51598-49-3) → β-yohimbine (549-84-8) + Yohimbine (146-48-5)

Guidance literature:

With sodium tetrahydroborate; nickel dichloride; In methanol; at 10 - 15 ℃;

DOI:10.1002/jlac.198619860407

upstream raw materials:

yohimbinic acid

corynanthine

3α-15α-20β-17α-hydroxylyohimbine-16α-carboxylic acid methyl ester

(+)-3,14-didehydroyohimbine

Downstream raw materials:

yohimbinic acid

(R)-2-methyl-2-(2,4,5-trichlorophenoxy)acetic acid

17α-benzoyloxy-yohimban-16α-carboxylic acid methyl ester

Indole-2-carboxylic acid

Refernces

• 1、 Blasko,Knight,Honty,Szantay. "Synthesis of yohimbines. 5. Enantioselective total synthesis of yohimbine and β-yohimbine antipodes". . p. 655 - 663. Retrieved 1986.
• 2、 Paciaroni, Nicholas G.,Norwood, Verrill M.,Garcia, Daniel E.,Huigens, Robert W.. "Microwave-enhanced, stereospecific ring-closure of medium-ring cyanamide ethers to yohimbine". . p. 1182 - 1185. Retrieved 2019.
• 3、 Herle, Bart,Wanner, Martin J.,Van Maarseveen, Jan H.,Hiemstra, Henk. "Total synthesis of (+)-yohimbine via an enantioselective organocatalytic Pictet-Spengler reaction". experimental part. p. 8907 - 8912. Retrieved 2011/12/21.
• 4、 -. "THERAPY FOR COMPLICATIONS OF DIABETES". . . Retrieved 2009/07/02.