Cas no 131-03-3 (Yohimban-16-carboxylicacid, 17-hydroxy-, methyl ester, (16b,17a,20a)-)

Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16β,17α,20α)- is a sterically defined yohimbane derivative with a carboxylate ester functionalization at the C-16 position and a hydroxyl group at C-17. Its rigid, stereospecific structure makes it a valuable intermediate in organic synthesis, particularly for alkaloid research and pharmaceutical applications. The compound’s defined stereochemistry ensures consistency in reactivity, aiding in the development of structurally complex molecules. Its methyl ester group enhances solubility in organic solvents, facilitating further derivatization. This compound is particularly useful in studies targeting adrenergic receptor modulators or exploring structure-activity relationships in yohimbane-based compounds.
Yohimban-16-carboxylicacid, 17-hydroxy-, methyl ester, (16b,17a,20a)- structure
131-03-3 structure
Product Name:Yohimban-16-carboxylicacid, 17-hydroxy-, methyl ester, (16b,17a,20a)-
CAS No:131-03-3
MF:C21H26N2O3
MW:354.442745685577
CID:168712
PubChem ID:643606
Update Time:2025-06-24

Yohimban-16-carboxylicacid, 17-hydroxy-, methyl ester, (16b,17a,20a)- Chemical and Physical Properties

Names and Identifiers

    • Yohimban-16-carboxylicacid, 17-hydroxy-, methyl ester, (16b,17a,20a)-
    • α-Yohimbine
    • alpha-Yohimbine
    • Methyl (16β,17α,20α)-17-hydroxyyohimban-16-carboxylate
    • KEOXIFENE
    • KEOXIFENE HYDROCHLORIDE
    • RALOXIFENE HCL
    • Rauwolscine
    • [ "" ]
    • 4-(2-amino-1-hydroxyethyl)-2-methoxyphenol hydrochloride(1:1)
    • methyl (16beta,17alpha,20alpha)-17-hydroxyyohimban-16-carboxylate
    • KBio2_004506
    • YOHIMBAN-16-CARBOXYLIC ACID, 17-HYDROXY-, METHYL ESTER, (16.BETA.,17.ALPHA.,20.ALPHA.)-
    • Spectrum2_000870
    • meso-Yohimbine
    • 131-03-3
    • Spectrum3_001761
    • YOHIMBINE, .ALPHA.-
    • methyl 17alpha-hydroxy-20alpha-yohimban-16beta-carboxylate
    • SCHEMBL244514
    • SR-01000075289-8
    • Rauwolscine;[3H]rauwolscine
    • Corynanthidine
    • DTXSID2045608
    • KBioSS_001938
    • Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (17alpha,20alpha)-
    • I+/--Yohimbin
    • NCGC00017260-05
    • 112350-93-3
    • SPBio_002613
    • Spectrum_001458
    • Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16beta,17alpha,20alpha)- (9CI)
    • methyl (1S,15S,18S,19S,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
    • KBio1_000414
    • NCGC00017260-06
    • UNII-T4LJ7LU45W
    • KBioGR_000938
    • IDI1_000414
    • SDCCGSBI-0051063.P003
    • T4LJ7LU45W
    • methyl hydroxy[?]carboxylate
    • GTPL136
    • KBio2_007074
    • .ALPHA.-YOHIMBINE [EP IMPURITY]
    • BRD-K77474816-003-05-9
    • Spectrum5_001121
    • yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16beta,17alpha,20alpha)-
    • SPBio_000919
    • KBio2_001938
    • .alpha.-Yohimbine
    • Tox21_110811
    • [3H]rauwolscine
    • SDCCGMLS-0066742.P001
    • DivK1c_000414
    • AB00514662
    • 20alpha-Yohimban-16beta-carboxylic acid, 17alpha-hydroxy-, methyl ester (8CI)
    • CAS-131-03-3
    • SR-01000075289
    • BPBio1_000434
    • Rauwolscine (6CI,7CI)
    • 17alpha-hydroxy-20alpha-yohimban-16beta-carboxylic acid methyl ester
    • 20-alpha-Yohimban-16-beta-carboxylic acid, 17-alpha-hydroxy-, methyl ester
    • Benz[g]indolo[2,3-a]quinolizine, yohimban-16-carboxylic acid deriv.
    • 17-alpha-Hydroxy-20-alpha-yohimban-16-beta-carboxylic acid methyl ester
    • BDBM50026636
    • CHEBI:48562
    • FS-10296
    • (1S,2S,4aS,13bS,14aS)-Methyl 2-hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate
    • NS00079316
    • AKOS032948426
    • YOHIMBINE HYDROCHLORIDE IMPURITY B [EP IMPURITY]
    • .ALPHA.-YOHIMBINE [MI]
    • GTPL223
    • -Yohimbine;Corynanthidine;Isoyohimbine
    • 5-AMINO-1-BENZOTHIOPHENE-2-CARBOXYLICACID
    • Prestwick0_000577
    • BSPBio_000394
    • Prestwick3_000577
    • BRD-K77474816-003-04-2
    • Isoyohimbine
    • Q7296272
    • CHEMBL10347
    • SR-01000075289-6
    • KBio3_002721
    • NINDS_000414
    • Prestwick1_000577
    • BRD-K77474816-003-09-1
    • BSPBio_003221
    • Prestwick2_000577
    • Lopac0_001093
    • Spectrum4_000319
    • DTXCID0025608
    • SR-01000075289-7
    • CCG-205170
    • METHYL 17.ALPHA.-HYDROXY-20.ALPHA.-YOHIMBAN-16.BETA.-CARBOXYLATE
    • Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16-beta,17-alpha,20-alpha)-
    • EINECS 205-006-9
    • Mesoyohimbine
    • BRD-K77474816-003-13-3
    • DA-57353
    • Inchi： 1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15+,17+,18+,19+/m1/s1
    • InChI Key： BLGXFZZNTVWLAY-DIRVCLHFSA-N
    • SMILES： O[C@H]1CC[C@@H]2CN3CCC4C5C=CC=CC=5NC=4[C@@H]3C[C@@H]2[C@@H]1C(=O)OC

Computed Properties

  • Exact Mass: 354.19400
  • Monoisotopic Mass: 354.194343
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 26
  • Rotatable Bond Count: 2
  • Complexity: 555
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 5
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.9
  • Topological Polar Surface Area: 65.6

Experimental Properties

  • Color/Form: Powder
  • Density: 1.31
  • Melting Point: 243-244°
  • Boiling Point: 543°Cat760mmHg
  • Flash Point: 282.2°C
  • PSA: 65.56000
  • LogP: 2.58500
  • pka: 6.34(at 25℃)
  • Specific Rotation: D19 -18° (pyridine); D19 -27° (abs alcohol)
  • Solubility: Soluble in chloroform, methanol \ ethanol, slightly soluble in water

Yohimban-16-carboxylicacid, 17-hydroxy-, methyl ester, (16b,17a,20a)- Security Information

  • Hazardous Material transportation number：UN 1544 6.1/PG 2
  • Safety Instruction： S22; S36/37/39; S45
  • Packing Group：II
  • Hazard Level：6.1(a)
  • Safety Term：6.1(a)
  • Packing Group：II
  • Risk Phrases：R23/24/25
  • HazardClass：6.1(a)
  • PackingGroup：II
  • Storage Condition：Store at room temperature, 2-8 ℃ is better

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Yohimban-16-carboxylicacid, 17-hydroxy-, methyl ester, (16b,17a,20a)- Related Literature

Related Categories

Additional information on Yohimban-16-carboxylicacid, 17-hydroxy-, methyl ester, (16b,17a,20a)-

Yohimban-16-carboxylic Acid, 17-Hydroxy-, Methyl Ester, (16b,17a,20a)-: A Comprehensive Overview

Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16b,17a,20a)- is a bioactive compound with the CAS number 131-03-3. This compound belongs to the class of yohimbane alkaloids and is derived from the bark of the *Pausinystalia johimbe* tree, commonly known as yohimbe. The compound's structure is characterized by a complex bicyclic framework with a carboxylic acid group at position 16 and a hydroxyl group at position 17. The methyl esterification at position 16 further enhances its chemical stability and bioavailability.

Recent studies have highlighted the potential of Yohimban-16-carboxylic acid in various therapeutic applications. For instance, research has demonstrated its ability to modulate neurotransmitter systems, particularly dopamine and serotonin pathways, which are critical in regulating mood and cognitive functions. This makes it a promising candidate for the development of novel antidepressant and anxiolytic agents.

The compound's stereochemistry plays a significant role in its pharmacological activity. The (16b,17a,20a) configuration ensures optimal interaction with cellular receptors, thereby enhancing its therapeutic efficacy. Advanced computational models have been employed to predict its binding affinity to various receptor sites, providing valuable insights into its mechanism of action.

In terms of synthesis and isolation, Yohimban-16-carboxylic acid can be obtained through a combination of extraction techniques from natural sources and chemical synthesis. Recent advancements in chromatographic techniques have enabled the efficient purification of this compound from plant extracts. Additionally, semi-synthetic approaches have been explored to modify its structure for enhanced pharmacokinetic properties.

One of the most intriguing aspects of Yohimban-16-carboxylic acid is its role in neuroprotection. Studies have shown that it exhibits antioxidant properties and can mitigate oxidative stress-induced neuronal damage. This has led to investigations into its potential use in treating neurodegenerative diseases such as Alzheimer's and Parkinson's disease.

The methyl ester derivative of Yohimban-16-carboxylic acid has also been studied for its improved solubility and absorption profile compared to the free acid form. This makes it more suitable for oral administration and enhances its bioavailability in vivo.

From an industrial perspective, the demand for Yohimban-16-carboxylic acid has increased due to its application in nutraceuticals and cosmeceuticals. Its ability to improve cognitive function and skin health has made it a valuable ingredient in health supplements and skincare products.

In conclusion, Yohimban-16-carboxylic acid, with CAS number 131-03-3, represents a versatile compound with diverse applications in medicine and health sciences. Ongoing research continues to uncover new insights into its mechanisms of action and therapeutic potential, positioning it as a key player in future drug development.

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