ChemBK
  • Home
  • Product Category

(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

Andrographolide

CAS: 5508-58-7

Molecular Formula: C20H30O5

  1. Home
  2. Product Category
  3. Biomedicine
  4. Chinese herbal extracts
  5. (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

(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 - 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

(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 - 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

(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 - 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

(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 - Upstream Downstream Industry

Raw MaterialsEthyl Alcohol

(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 - 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]

(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 - 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

(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 - 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

(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 - 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
(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
Supplier List
Shanghai Yuanye Bio-Technology Co., Ltd.
Featured ProductsMultiple SpecificationsSpot supply
Product Name: Andrographolide Visit Supplier Webpage Request for quotation
CAS: 5508-58-7
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409 Click to send a QQ message
Wechat: 18301782025
Nantong Reform Petro-Chemical CO., LTD.
Spot supply
Product Name: Andrographolide Request for quotation
CAS: 5508-58-7
Tel: +86-17551318830
Email: r@reformchem.com­
Mobile: +86-17551318830
QQ: 3785839865 Click to send a QQ messageSend QQ message
Jiangsu Pules Biotechnology Co.,Ltd.
Product Name: Andrographolide Request for quotation
CAS: 5508-58-7
Tel: 17505222756
Email: pules.cn@gmail.com
Mobile: +86-17551318830
Wechat: 17505222756
Hubei YoungXin Pharmaceutical Tech Co.,Ltd.
Spot supply
Product Name: Andrographolide Visit Supplier Webpage Request for quotation
CAS: 5508-58-7
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052 Click to send a QQ message
Wechat: 15671228036
Guangzhou Yuanda New Material Co.,Ltd
Multiple Specifications
Product Name: Andrographolide Request for quotation
CAS: 5508-58-7
Tel: +86 19849939632
Email: 2470479589@qq.com
Mobile: +86 19849939632
QQ: 2470479589 Click to send a QQ message
Wechat: +86 19849939632
Hefei TNJ Chemical Industry Co.,Ltd.
Product Name: Andrographolide Request for quotation
CAS: 5508-58-7
Tel: 0086-551-65418684
Email: sales@tnjchem.com
　　　　 info@tnjchem.com
Mobile: 0086 189 4982 3763
QQ: 2881500840 Click to send a QQ message
Wechat: 0086 189 4982 3763
WhatsApp: 0086 189 4982 3763
Product List: View Catalog
Shanghai Worldyang Chemical Co.,Ltd.
Product Name: Andrographolide Request for quotation
CAS: 5508-58-7
Tel: +86-21-56795779
Email: charles7788@worldyachem.com
Mobile: +86-13651600618
QQ: 2850607228 Click to send a QQ message
Wechat: 13651600618
WhatsApp: +8613651600618
Changsha Staherb Natural Ingredients Co., Ltd.,
Spot supply
Product Name: Andrographolide Visit Supplier Webpage Request for quotation
CAS: 5508-58-7
Tel: +86-(0)731-84213302
Email: sales@staherb.cn
Mobile: +86 13875855783
QQ: 484702402 Click to send a QQ message
WhatsApp: +86 18374838656
Linkedin: +86 18374838656
Shanghai Yuanye Bio-Technology Co., Ltd.
Featured ProductsMultiple SpecificationsSpot supply
Product Name: Andrographolide Visit Supplier Webpage Request for quotation
CAS: 5508-58-7
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409 Click to send a QQ message
Wechat: 18301782025
Nantong Reform Petro-Chemical CO., LTD.
Spot supply
Product Name: Andrographolide Request for quotation
CAS: 5508-58-7
Tel: +86-17551318830
Email: r@reformchem.com­
Mobile: +86-17551318830
QQ: 3785839865 Click to send a QQ messageSend QQ message
Jiangsu Pules Biotechnology Co.,Ltd.
Product Name: Andrographolide Request for quotation
CAS: 5508-58-7
Tel: 17505222756
Email: pules.cn@gmail.com
Mobile: +86-17551318830
Wechat: 17505222756
Hubei YoungXin Pharmaceutical Tech Co.,Ltd.
Spot supply
Product Name: Andrographolide Visit Supplier Webpage Request for quotation
CAS: 5508-58-7
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052 Click to send a QQ message
Wechat: 15671228036
Guangzhou Yuanda New Material Co.,Ltd
Multiple Specifications
Product Name: Andrographolide Request for quotation
CAS: 5508-58-7
Tel: +86 19849939632
Email: 2470479589@qq.com
Mobile: +86 19849939632
QQ: 2470479589 Click to send a QQ message
Wechat: +86 19849939632
Hefei TNJ Chemical Industry Co.,Ltd.
Product Name: Andrographolide Request for quotation
CAS: 5508-58-7
Tel: 0086-551-65418684
Email: sales@tnjchem.com
　　　　 info@tnjchem.com
Mobile: 0086 189 4982 3763
QQ: 2881500840 Click to send a QQ message
Wechat: 0086 189 4982 3763
WhatsApp: 0086 189 4982 3763
Product List: View Catalog
Shanghai Worldyang Chemical Co.,Ltd.
Product Name: Andrographolide Request for quotation
CAS: 5508-58-7
Tel: +86-21-56795779
Email: charles7788@worldyachem.com
Mobile: +86-13651600618
QQ: 2850607228 Click to send a QQ message
Wechat: 13651600618
WhatsApp: +8613651600618
Changsha Staherb Natural Ingredients Co., Ltd.,
Spot supply
Product Name: Andrographolide Visit Supplier Webpage Request for quotation
CAS: 5508-58-7
Tel: +86-(0)731-84213302
Email: sales@staherb.cn
Mobile: +86 13875855783
QQ: 484702402 Click to send a QQ message
WhatsApp: +86 18374838656
Linkedin: +86 18374838656
View History
(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
Raw Materials for (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
Ethyl Alcohol
  • Home
  • Product Category

© 2015, 2023 ChemBK.com All Rights Reserved | Build: 20230617001