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Basic Information

Molecular Structure:
CAS No.:	5508-58-7
Name:	Andrographolide
Article Data:	1

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
Appearance:	powder
Hazard Symbols:	Xn
Risk Codes:	20/21/22-36/37/38
Safety:	22-24/25-36-26
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

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
With ethanol; platinum Hydrogenation;

: 5508-58-7
andrographolide

: 4176-96-9
isoandrographolide

Conditions

Conditions	Yield
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

Conditions	Yield
With hydrogenchloride; acetic acid

: 5508-58-7
andrographolide

selenium: selenium

: 2131-43-3
1,2,5,6-tetramethylnaphthalene

Conditions

Conditions	Yield
at 320℃;

: 110-86-1
pyridine

: 108-24-7
acetic anhydride

: 5508-58-7
andrographolide

di-O-acetyl-anhydroandrographolide: di-O-acetyl-anhydroandrographolide

...Expand

: 127-09-3
sodium acetate

: 108-24-7
acetic anhydride

: 5508-58-7
andrographolide

di-O-acetyl-anhydroandrographolide: di-O-acetyl-anhydroandrographolide

...Expand

: 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

...Expand

: 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

...Expand

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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: Harmful Xn
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.