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Andrographolide(CAS No. 5508-58-7)

Andrographolide C20H30O5 (cas 5508-58-7) Molecular Structure

5508-58-7 Structure

Identification and Related Records

【Name】
Andrographolide
【Iupac name】
(3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,
8a-dimethyl-2-methylidene-3,4,4a,6,7,
8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one
【CAS Registry number】
5508-58-7
【Synonyms】
2(3H)-Furanone, 3-[2-[(1R,4aS,5R,6R,8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-, (3E,4S)-
2(3H)-Furanone, 3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-, (1R-(1-alpha(E(S*)),4a-beta,5-alpha,6-alpha,8a-alpha))-
(3E)-3-[2-[(1S,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decalin-1-yl]ethylidene]-4-hydroxy-oxolan-2-one
Andrographis
【EINECS(EC#)】
226-852-5
【Molecular Formula】
C20H30O5 (Products with the same molecular formula)
【Molecular Weight】
350.45
【Inchi】
InChI=1/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14-,15?,16?,17?,19+,20?/m1/s1
【Canonical SMILES】
CC12CCC(C(C1CCC(=C)C2CC=C3C(COC3=O)O)(C)CO)O
【Isomers smiles】
C[C@@]12CC[C@H]([C@@]([C@H]1CCC(=C)[C@H]2C/C=C/3\[C@@H](COC3=O)O)(C)CO)O
【MOL File】
5508-58-7.mol

Chemical and Physical Properties

【Appearance】
powder
【Density】
1.21g/cm3
【Melting Point】
229-232℃
【Boiling Point】
557.3 °C at 760 mmHg
【Refractive Index】
1.567
【Flash Point】
557.3 °C at 760 mmHg
【Alpha】
-126 o (C=1.5,HAC)
【Solubilities】
Insoluble
【HS Code】
29322980
【Storage temp】
Keep tightly closed. Store in a cool dry place.
【Computed Properties】
Molecular Weight:350.4492 [g/mol]
Molecular Formula:C20H30O5
XLogP3-AA:2.2
H-Bond Donor:3
H-Bond Acceptor:5
Rotatable Bond Count:3
Exact Mass:350.209324
MonoIsotopic Mass:350.209324
Topological Polar Surface Area:87
Heavy Atom Count:25
Formal Charge:0
Complexity:597
Isotope Atom Count:0
Defined Atom Stereocenter Count:6
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:1
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:4
Feature 3D Donor Count:3
Feature 3D Ring Count:3
Effective Rotor Count:5
Conformer Sampling RMSD:0.8
CID Conformer Count:10

Safety and Handling

【Hazard Codes】
Xn
【Risk Statements】
R20/21/22
【Safety Statements 】
S22;S24/25
【Safety】

Hazard Codes:?HarmfulXn
Risk Statements: 20/21/22-36/37/38
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-36-26
S22:Do not breathe dust.?
S24/25:Avoid contact with skin and eyes.?
S36:Wear suitable protective clothing.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
RTECS: LU3490750

【Specification】

? Andrographis , with CAS number of 5508-58-7, can be called 2(3H)-Furanone, 3-[2-[(1R,4aS,5R,6R,8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-, (3E,4S)- ; Madecassic acid ; 2(3H)-Furanone, 3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-, (1R-(1-alpha(E(S*)),4a-beta,5-alpha,6-alpha,8a-alpha))- ; 3-[2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenenaphthyl]ethylidene]dihydro-4-hydroxyfuran-2(3H)-one ; (3E,4S)-3-[2-[(1S,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decalin-1-yl]ethylidene]-4-hydroxy-oxolan-2-one .?It is antibacterial and anti-inflammatory. The application of Andrographis (CAS NO.5508-58-7) in the treatment of bacterial dysentery, acute gastroenteritis, mumps, tonsillitis, laryngitis, upper respiratory tract infection infections.

Use and Manufacturing

【Usage】

May boost immune response.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Substances that reduce or suppress INFLAMMATION.
- Anti-inflammatory agents that are not steroids. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They are used primarily in the treatment of chronic arthritic conditions and certain soft tissue disorders associated with pain and inflammation. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. Certain NSAIDs also may inhibit lipoxygenase enzymes or TYPE C PHOSPHOLIPASES or may modulate T-cell function. (AMA Drug Evaluations Annual, 1994, p 1814-5)
- Substances that are destructive to protozoans.
- Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.
- Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
【Therapeutic Uses】
Andrographolide is a labdane diterpenoid. Andrographolide is the main bioactive component isolated from the medicinal plant Andrographis paniculata. Andrographolide showed significant antihepatotoxic action in P. berghei K173- induced hepatic damage in M. natalensis. Andrographolide inhibits tumor necrosis factor-α (TNF-α)-induced intercellular adhesion mol.-1 (ICAM-1) expression and adhesion of HL-60 cells onto human umbilical vein endothelial cells (HUVEC), which are associated with inflammatory diseases. These findings suggest that Andrographolide may have potential as a cardiovascular-protective agent.

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