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UNCARINE D is an alkaloid compound isolated from the leaves of Mitragyna speciosa, characterized by its unique structure with a cis DIE ring junction and a conformation that causes the oxindole ring to deshield the ester methoxyl group. It is known for its immunomodulating, anti-inflammatory, and anti-cancer properties, which are attributed to the presence of tetra/pentacyclic oxindole alkaloids.

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  • Spiro[3H-indole-3,6'(4'aH)-[1H]pyrano[3,4-f]indolizine]-4'-carboxylicacid, 1,2,5',5'a,7',8',10',10'a-octahydro-1'-methyl-2-oxo-, methyl ester,(1'S,3S,4'aS,5'aR,10'aS)-

    Cas No: 4697-68-1

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  • Spiro[3H-indole-3,6'(4'aH)-[1H]pyrano[3,4-f]indolizine]-4'-carboxylicacid, 1,2,5',5'a,7',8',10',10'a-octahydro-1'-methyl-2-oxo-, methyl ester,(1'S,3S,4'aS,5'aR,10'aS)-

    Cas No: 4697-68-1

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  • Spiro[3H-indole-3,6'(4'aH)-[1H]pyrano[3,4-f]indolizine]-4'-carboxylicacid, 1,2,5',5'a,7',8',10',10'a-octahydro-1'-methyl-2-oxo-, methyl ester,(1'S,3S,4'aS,5'aR,10'aS)-

    Cas No: 4697-68-1

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  • 4697-68-1 Structure
  • Basic information

    1. Product Name: UNCARINE D
    2. Synonyms: SPECIOPHYLLINE;UNCARINE D;(3β,7S,20α)-19α-Methyl-2-oxoformosanan-16-carboxylic acid methyl ester;Nsc113094;Speciophylline (Uncarine D);Uncarin D
    3. CAS NO:4697-68-1
    4. Molecular Formula: C21H24N2O4
    5. Molecular Weight: 368.43
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 4697-68-1.mol
  • Chemical Properties

    1. Melting Point: 183~184℃
    2. Boiling Point: 555.2 °C at 760 mmHg
    3. Flash Point: 289.6 °C
    4. Appearance: /
    5. Density: 1.33
    6. Vapor Pressure: 2.3E-12mmHg at 25°C
    7. Refractive Index: 1.635
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: 13.56±0.60(Predicted)
    11. CAS DataBase Reference: UNCARINE D(CAS DataBase Reference)
    12. NIST Chemistry Reference: UNCARINE D(4697-68-1)
    13. EPA Substance Registry System: UNCARINE D(4697-68-1)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 4697-68-1(Hazardous Substances Data)

4697-68-1 Usage

Uses

Used in Pharmaceutical Industry:
UNCARINE D is used as an immunomodulating agent for its ability to modulate the immune system and enhance the body's defense mechanisms against various diseases and infections.
Used in Anti-inflammatory Applications:
UNCARINE D is used as an anti-inflammatory agent for its potential to reduce inflammation and alleviate pain associated with various conditions, such as arthritis and other inflammatory disorders.
Used in Anticancer Applications:
UNCARINE D is used as an anti-cancer agent for its potential to inhibit the growth and progression of cancer cells. It may also demonstrate synergistic effects when combined with conventional chemotherapeutic drugs, enhancing their efficacy and overcoming drug resistance in cancer treatment.
Used in Drug Delivery Systems:
To improve the bioavailability and therapeutic outcomes of UNCARINE D, novel drug delivery systems have been developed. These systems, which may include organic and metallic nanoparticles, aim to enhance the delivery and effectiveness of UNCARINE D in treating various medical conditions, including cancer and inflammatory disorders.

References

Beckett et al., Sci. Pharm., Froc., 25th (1965)

Check Digit Verification of cas no

The CAS Registry Mumber 4697-68-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,6,9 and 7 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 4697-68:
(6*4)+(5*6)+(4*9)+(3*7)+(2*6)+(1*8)=131
131 % 10 = 1
So 4697-68-1 is a valid CAS Registry Number.
InChI:InChI=1/C21H24N2O4/c1-12-14-10-23-8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-27-12)19(24)26-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)/t12-,13-,14-,18+,21-/m0/s1

4697-68-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name UNCARINE D

1.2 Other means of identification

Product number -
Other names Speciophyllin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4697-68-1 SDS

4697-68-1Relevant articles and documents

Analysis of the kinetics of isomerization of spiro oxindole alkaloids

Laus, Gerhard,Broessner, Dagmar,Senn, Gilbert,Wurst, Klaus

, p. 1931 - 1936 (2007/10/03)

The isomerization of the spiro oxindole alkaloids mitraphylline, isomitraphylline, pteropodine, isopteropodine, speciophylline and uncarine F in water has been studied at several temperatures and the rate coefficients have been determined. The effect of pH on the rate of reaction and the equilibrium composition has been investigated. The rate coefficients in water and in organic solvents correlate satisfactorily with the Dimroth-Reichardt solvent polarity parameter. The present results support the existence of a zwitterionic intermediate stabilized by polar solvents and show that protonation of the alkaloids inhibits the isomerization. The crystal structure of pteropodine has been determined.

Alkaloids of Mitragyna parvifolia (Roxb) Korth. and their Transformations

Chatterjee, A.,Dhara, K. P.,Banerji, J.

, p. 1360 - 1363 (2007/10/02)

From the basic fractions of the leaves of Mitragyna parvifolia (Roxb) Korth, three oxindole alkaloids, mitraphylline, isomitraphylline and speciophylline Nb-oxide were isolated.A novel method has been developed for the transformation of mitraphylline, the major alkaloid of this species, to the corresponding heteroyohimbinoid base, ajmalicine without disturbing any chiral centre.Mitraphylline Nb-methoiodide, when treated with triethyloxonium fluoroborate, was converted to its corresponding imino-ether which on reduction with sodium borohydride in acetic acid furnished ajmalicine Nb-methoiodide.The latter could be transformed to ajmalicine by conventional procedure.

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