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Andrographolid

Andrographolide

CAS: 5508-58-7

Molecular Formula: C20H30O5

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Andrographolid - Names and Identifiers

Name Andrographolide
Synonyms NSC 383468
Andrographolid
Andrographolide
UNII-410105JHGR
5-alpha,6-alpha,8a-alpha))-t
andrographolide,14-deoxy 11,12-didehydro
ent-(3β,12E,14R)-3,14,19-Trihydroxy-8(17),12-labdadien-16,15-olide
2(3h)-furanone,3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-met
3-(2-(Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenenaphthyl)ethylidene)dihydro-4-hydroxyfuran-2(3H)-one
4-hydroxy-3-{2-[6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidenedecahydronaphthalen-1-yl]ethylidene}dihydrofuran-2(3H)-one
(S)-3-[(E)-2-[[(1R,4aα)-Decahydro-6β-hydroxy-5β-hydroxymethyl-5,8aβ-dimethyl-2-methylenenaphthalen]-1β-yl]ethylidene]dihydro-4-hydroxy-2(3H)-furanone
(3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-1,2,3,4,4a,5,6,7,8,8a-Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenenaphthalene-1-yl]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-(1-alpha(E(S*)),4a-beta,5- alpha,6-alpha,8a-alpha))-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))-
CAS 5508-58-7
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
InChIKey BOJKULTULYSRAS-QPSYGYIJSA-N

Andrographolid - Physico-chemical Properties

Molecular FormulaC20H30O5
Molar Mass350.45
Densityd421 1.2317
Melting Point229-232 °C (lit.)
Boling Point557.3±50.0 °C(Predicted)
Specific Rotation(α)-126 º (c=1.5,HAc)
Flash Point195.5°C
Solubility Soluble in methanol, ethanol and acetone, slightly soluble in chloroform, ether, insoluble in water, petroleum ether and benzene.
Vapor Presure9.64E-15mmHg at 25°C
AppearanceWhite prismatic or flaky crystals (ethanol or methanol)
ColorOff-white
Maximum wavelength(λmax)['223nm(MeOH)(lit.)']
Merck14,633
BRN42762
pKa12.36±0.20(Predicted)
Storage Condition2-8°C
StabilityStable for 2 years from date of purchsae as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
Refractive Index1.567
MDLMFCD07778082
Physical and Chemical PropertiesWhite square or rectangular crystal. Melting point 224-230 °c (decomposition). Soluble in boiling ethanol, slightly soluble in methanol or ethanol, very slightly soluble in chloroform, insoluble in water or ether. No odor, extremely bitter taste.
UseIt has the effect of clearing heat and detoxification, antibacterial and anti-inflammatory, and is used for the treatment of Upper Respiratory Infections, bacillary dysentery, anti-HIV and other diseases

Andrographolid - Risk and Safety

Hazard SymbolsXn - Harmful
Harmful
Risk CodesR20/21/22 - Harmful by inhalation, in contact with skin and if swallowed.
R36/37/38 - Irritating to eyes, respiratory system and skin.
Safety DescriptionS22 - 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 Germany3
RTECSLU3490750
HS Code29322980

Andrographolid - Upstream Downstream Industry

Raw MaterialsEthyl Alcohol

Andrographolid - Reference

Reference
Show more
1. Cui Dandan, Zeng Lingjie, Huang Jialing, etc. Quality Grade Evaluation of Andrographis paniculata based on principal component clustering and PLS regression analysis [J]. Chinese herbal medicine, 2019.
2. Wei Dongyan, Wei Dongmei, Teng Li. Effects of Andrographolide on proliferation, apoptosis and cell cycle of human cervical cancer SiHa cells [J]. China Maternal and Child Health Care, 2019, 034(014):3341-3344.
3. Yu-yu, Tang, Weiping. Effects of Andrographolide on proliferation and apoptosis of human tongue squamous cell carcinoma Tca8113 cells [J]. Chongqing Medical Journal, 2014, 25 (14):67-69 72.
4. Wei Dongyan, Wei Dongmei, Teng Li. Anti-tumor effect of Andrographolide on cervical cancer U14 tumor-bearing mice [J]. Chinese traditional medicines, 2020, v.42(02):211-214.
5. Wang Jingxian, Li Wen, Chen Ting, etc. Preparation and evaluation of Andrographolide nanosuspension [J]. Journal of Nanjing University of Traditional Chinese Medicine, 2017, 33(003):313-316.
6. Meng Hui, Xu Yong. Preparation and dissolution evaluation of Andrographolide self-emulsifying soft capsules [J]. Journal of Pharmaceutical Practice, 2010, 28(3):184-185.
7. Shao Xiaoting, Zhang Yu, Guo Zijin, etc. Preparation of hyaluronic acid-Phenylboronic acid nanoparticles loaded with diterpene Lactones from Andrographis paniculata [J]. Chinese traditional medicines, 2019, 041(011):2553-560.
8. Shao Yanhua, Wang Jiangang, Lai Xiaoping, etc. Study on HPLC fingerprint of diterpene Lactones from Andrographis paniculata [J]. Chinese herbal medicines, 2014, 37(2):219-223.
9. Zeng Wu Jing, Xu Ling, He Qiu Ling, etc. Agronomic traits of Andrographis paniculata and their correlation with diterpene lactones [J]. Chinese Journal of Traditional Chinese Medicine, 2019, 26 (15).
10. Huang Jialing, Zeng Lingjie, Cui Dandan, Chen yuanxia, Zhang Xiaoyuan, Zhang Junyan. Correlation between Andrographis paniculata grade and leaf-stem ratio, extract and lactones [J]. Chinese traditional medicines, 2020,42(10):2675-2679.
11. Liu, G., & Liu, G. (2018). Andrographolide inhibitors and industries cell cycle arrest and apotosis in human melanoma cells. Oncology Letters, 15, 5301-5305. https://doi.org/10.3892/ol.2018.7941
12. [IF=2.311] Guo Liu et al."Andrographolide inhibits proliferation and induces cell cycle arrest and apoptosis in human melanoma cells."Oncol Lett. 2018 Apr;15(4):5301-5305
13. [IF=0] Ying Liu et al."Andrographolide Induces Autophagic Cell Death and Inhibits Invasion and Metastasis of Human Osteosarcoma Cells in An Autophagy-Dependent Manner."Cell Physiol Biochem. 2017;44(4):1396-1410
14. [IF=4.101] Yan Li et al."Protective effects of andrographolide against cerebral ischemia‑reperfusion injury in mice."Int J Mol Med. 2021 Oct;48(4):1-13
15. [IF=1.287] Xiaofei Li et al."Andrographolide enhanced radiosensitivity by downregulating glycolysis via the inhibition of the PI3K-Akt-mTOR signaling pathway in HCT116 colorectal cancer cells:."J Int Med Res. 2020;48(8):
16. [IF=2.441] Loureiro Damasceno et al.Andrographis paniculata Formulations: Impact on Diterpene Lactone Oral Bioavailability.European Journal Of Drug Metabolism And Pharmacokinetics.2021 Nov 23
17. [IF=4.932] Ronglong Luo et al."Andrographolide attenuates Mycoplasma gallisepticum-induced inflammation and apoptosis by the JAK/PI3K/AKT signal pathway in the chicken lungs and primary alveolar type II epithelial cells."INTERNATIONAL IMMUNOPHARMACOLOGY. 2022 Aug;109
18. [IF=5.811]

Andrographolid - Nature

Open Data Verified Data

colorless square, rectangular or prismatic crystals. Melting point 230~231 °c (decomposition). No odor, extremely bitter taste. Insoluble in water and ether, slightly soluble in methanol, ethanol and chloroform, soluble in hot ethanol and glacial acetic acid. The relative density (d21) is 1- 231 and the specific optical rotation is -124.6. ~-128.6. (Glacial acetic acid). It is usually a triacetyl derivative with a melting point of 126 to 127 °c.

Last Update：2024-01-02 23:10:35

Andrographolid - Preparation Method

Open Data Verified Data

Usually the stems and leaves of Andrographis paniculata are extracted as raw materials. The crude powder of heart lotus stem and leaf was cold-soaked with 95% ethanol, and the cold extract was decolorized by reflux with activated carbon, filtered while hot, then the filtrate was concentrated to about 1/5 of the original volume, then cold water was added, and then the crystals were left to stand, the crude Andrographolide was obtained by filtration. A more pure product was then obtained by recrystallization from 95% ethanol. If the pure product is to be prepared, it can be purified according to the following method. The above product was washed with chloroform cold dip (oxygen Andrographolide can be removed), and the insoluble matter was recrystallized from 15 times the amount (V/W) of 95% ethanol to obtain a pure product.

Last Update：2022-01-01 11:15:03

Andrographolid - Use

Open Data Verified Data

Andrographolide is antibacterial, anti-inflammatory, heat-clearing and antidotal. Suitable for the treatment of bacterial dysentery, acute gastroenteritis, mumps, tonsillitis, Upper Respiratory Infections disease.

Last Update：2022-01-01 11:15:04
Andrographolid
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View History
Andrographolid
Compound additive
4-morpholin-4-ylaniline hydrochloride
Acetamide, 2-cyano-N-[1-(4-ethylphenyl)ethyl]- (9CI)
Teksanol
BIS(4-METHACRYLOYLTHIOPHENYL) SULFIDE
L-alphs-Amino-3-indolepropionic acid
胆固醇杂质
VINYLETHYLDIMETHYLSILANE
单醋酸甘油酯
Raw Materials for Andrographolid
Ethyl Alcohol
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