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5508-58-7

Basic Information
CAS No.: 5508-58-7
Name: Andrographolide
Article Data: 1
Cas Database
Molecular Structure:
Molecular Structure of 5508-58-7 (Andrographolide)
Formula: C20H30O5
Molecular Weight: 350.45
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: 226-852-5
Density: 1.21 g/cm3
Melting Point: 229-232 °C(lit.)
Boiling Point: 557.3 °C at 760 mmHg
Flash Point: 195.5 °C
Solubility: N/A
Appearance: powder
Hazard Symbols: HarmfulXn
Risk Codes: 20/21/22-36/37/38
Safety: 22-24/25-36-26
Transport Information: N/A
PSA: 86.99000
LogP: 1.96260
Synthetic route
110-86-1

pyridine

76-83-5

trityl chloride

5508-58-7

andrographolide

ent-3β,15-dihydroxy-19-trityloxy-labda-8(20),11ξ,13t-trien-16-oic acid-15-lactone

108-24-7

acetic anhydride

5508-58-7

andrographolide

79233-05-9

ent-(14Ξ)-3β,14,19-triacetoxy-15-hydroxy-labda-8(20),12ξ-dien-16-oic acid-lactone

Conditions
ConditionsYield
With zinc(II) chloride
With sulfuric acid
5508-58-7

andrographolide

ent-(13Ξ,14Ξ)-3β,14,15,19-tetrahydroxy-8ξH-labdan-16-oic acid-15-lactone

Conditions
ConditionsYield
With ethanol; platinum Hydrogenation;
5508-58-7

andrographolide

4176-96-9

isoandrographolide

Conditions
ConditionsYield
With hydrogenchloride
5508-58-7

andrographolide

ent-(12Ξ,13Ξ,14Ξ)-8,12-dichloro-3β,14,15,19-tetrahydroxy-8ξH-labdan-16-oic acid-15-lactone

Conditions
ConditionsYield
With hydrogenchloride; acetic acid
5508-58-7

andrographolide

selenium

selenium

2131-43-3

1,2,5,6-tetramethylnaphthalene

Conditions
ConditionsYield
at 320℃;
110-86-1

pyridine

108-24-7

acetic anhydride

5508-58-7

andrographolide

di-O-acetyl-anhydroandrographolide

di-O-acetyl-anhydroandrographolide

127-09-3

sodium acetate

108-24-7

acetic anhydride

5508-58-7

andrographolide

di-O-acetyl-anhydroandrographolide

di-O-acetyl-anhydroandrographolide

5508-58-7

andrographolide

aqueous Ba(OH)2

aqueous Ba(OH)2

A

ent-(14Ξ)-3β.14.15.19-tetrahydroxy-labdadien-(8(20).12ξ)-oic acid-(16)

B

isoandrographolic acid

isoandrographolic acid

5508-58-7

andrographolide

aqueous ethanolic KOH

aqueous ethanolic KOH

A

ent-(14Ξ)-3β.14.15.19-tetrahydroxy-labdadien-(8(20).12ξ)-oic acid-(16)

B

isoandrographolic acid

isoandrographolic acid

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Chemistry

Molecular Structure of Andrographis (CAS NO.5508-58-7):

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 
Empirical Formula: C20H30O5
Molecular Weight: 350.4492
H bond acceptors: 5
H bond donors: 3
Freely Rotating Bonds: 6
Polar Surface Area: 53.99 Å2
Index of Refraction: 1.567
Molar Refractivity: 94.13 cm3
Molar Volume: 287.9 cm3
Surface Tension: 51.9 dyne/cm
Density: 1.21 g/cm3
Flash Point: 195.5 °C
Enthalpy of Vaporization: 96.43 kJ/mol
Boiling Point: 557.3 °C at 760 mmHg
Vapour Pressure: 9.64E-15 mmHg at 25°C
Melting point: 229-232 °C(lit.)
alpha: -126 o (c=1.5,HAc)
Merck: 13,638
EINECS: 226-852-5
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
Smiles
C1[C@@H]([C@@]([C@@H]2CCC(=C)[C@H](C\C=C3\C(OC[C@@H]3O)=O)[C@@]2(C)C1)(C)CO)O
Product Categories: Di-Terpenoids; Asymmetric Synthesis; Chiral Building Blocks; Complex Molecules

Production

  Andrographis (CAS NO.5508-58-7) is derived from the leaves of a lactone.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 11460mg/kg (11460mg/kg)   Indian Journal of Medical Research. Vol. 92, Pg. 276, 1990.

Safety Profile

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

Standards and Recommendations

Substance: Andrographis Paniculata
Content (%) of Madecassic acid: 100%

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.