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 No.: 5508-58-7

Molecular Weight：350.4492

Modify Date.: 2022-11-29 05:26

Introduction: Andrographolide is the bitter principle, a colorless and neutral crystalline substance. It is the major labdane diterpenoid isolated from Andrographis paniculate. It exhibits antiviral, anti-inflammatory, and anticancer activities. The underlying mechanism is the inhibition of the mitogen-activated protein kinase/extracellular signal-regulated kinase (MAPK/ERK) signaling (specifically p38 MAPK/ERK1/2) pathway and downstream transcription factors such as nuclear factor kappa B (NF-κB) and nuclear factor of activated T cells (NFAT). Andrographolide is also confirmed with chemopreventive effects against and the inhibitory effects on cancer cell growth in breast, colon, epidermoid, gastric, liver, leukemia, myeloma, peripheral blood lymphocytes, and prostate cancers.Andrographolide has been used for liver complaints and fever, and as an anti-inflammatory and immunostimulant. Andrographolide exerts anti-growth and pro-apoptotic effects on human rheumatoid arthritis fibroblast- like synoviocytes, the main cellular constituent of pannus, that combined with a massive infiltration of lymphocytes and macrophages, invades and destroys the local articular structure. Thereby, andrographolide is proposed to be used in Rheumatoid Arthritis and other autoimmune diseases. View more+

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1. Names and Identifiers

1.1 Name: Andrographolide
1.2 Synonyms: (3E)-3-[2-[(1R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxy-2-oxolanone (3E)-3-[2-[(1S,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decalin-1-yl]ethylidene]-4-hydroxy-oxolan-2-one (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-2(3H)-furanone 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))- 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- 2(3H)-Furanone, 3-[2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-, [1R-[1α[E(S*)],4aβ,5α,6α,8aα]]- 226-852-5 3-[2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenenaphthyl]ethylidene]dihydro-4-hydroxyfuran-2(3H)-one 3-dehydroandrographolide or 19-dehydroandrographolide? p. 1388 4-Hydroxy-3-{2-[6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydro-1-naphthalenyl]ethylidene}dihydro-2(3H)-furanone 5β,9βH,10α-Labda-8(20),12-dien-16-oic acid, 3α,14,15,18-tetrahydroxy-, γ-lactone Andrographis Andrographiside aglycon Andrographolid

1.3 CAS No.: 5508-58-7

1.4 CID: 5318517

1.5 EINECS(EC#): 226-852-5

1.6 Molecular Formula: C20H30O5 (isomer)

1.7 Inchi: InChI=1S/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

1.8 InChkey: BOJKULTULYSRAS-OTESTREVSA-N

1.9 Canonical Smiles: CC12CCC(C(C1CCC(=C)C2CC=C3C(COC3=O)O)(C)CO)O

1.10 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

2. Properties

2.1 Density: 1.21

2.1 Melting point: 229-232℃

2.1 Boiling point: 557.3 °C at 760 mmHg

2.1 Refractive index: 1.567

2.1 Flash Point: 557.3 °C at 760 mmHg

2.1 Precise Quality: 350.20900

2.1 PSA: 86.99000

2.1 logP: 1.96260

2.1 Λmax: 223nm(MeOH)(lit.)

2.2 Appearance: powder

2.3 Chemical Properties: colorless Plates

2.4 pKa: 12.36±0.20(Predicted)

2.5 Water Solubility: Insoluble

2.6 StorageTemp: Keep tightly closed. Store in a cool dry place.

3. Use and Manufacturing

3.1 Definition: ChEBI: A labdane diterpenoid isolated from the leaves and roots of Andrographis paniculata that exhibits anti-HIV, anti-inflammatory and antineoplastic properties.

3.2 Usage: May boost immune response.

4. Safety and Handling

4.1 Hazard Codes: Xn

4.1 Risk Statements: R20/21/22

4.1 Safety Statements: S22;S24/25

4.1 Hazard Declaration: H315

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

4.1 WGK Germany: 3

4.1 RTECS: LU3490750

4.1 Safety: Hazard Codes:?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

4.2 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.

4.3 Toxicity

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.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Computational chemical data

Molecular Weight: 350.4492g/mol
Molecular Formula: C₂₀H₃₀O₅
Compound Is Canonicalized: True
XLogP3-AA: 2.2
Exact Mass: 350.20932405
Monoisotopic Mass: 350.20932405
Complexity: 597
Rotatable Bond Count: 3
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 5
Topological Polar Surface Area: 87
Heavy Atom Count: 25
Defined Atom Stereocenter Count: 6
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB4OAAAAAAAAAAAAAAAAAAAASAAAAAwYAAAAAAAAADAAAAAGgAACAAADxSggAICCAAABgCIAiDSCAAAAAAgAAAACAEAAEgBFBYAIQACUAAF4AALMYOCwPAPgAAAAAAAAABAAAYAADAAAAAAAAAAAA==

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8. Realated Product Infomation

79233-15-1 ANDROGRAPHOLIDE, DEOXY-

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