Neoandrographolide

Base Information

• Chemical Name: Neoandrographolide
• CAS No.: 27215-14-1
• Molecular Formula: C26H40O8
• Molecular Weight: 480.599
• UNII: XBY0Z806J2
• DSSTox Substance ID: DTXSID80904895
• Nikkaji Number: J17.273A
• Wikidata: Q27293767
• Metabolomics Workbench ID: 138045
• ChEMBL ID: CHEMBL480853
• Mol file: 27215-14-1.mol

Synonyms:neoandrographolide

Chemical Property of Neoandrographolide

Chemical Property:

• Appearance/Colour: Colorless columnar crystal
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 167-168 °C
• Refractive Index: 1.576
• Boiling Point: 668.1 °C at 760 mmHg
• PKA: 12.93±0.70(Predicted)
• Flash Point: 220.1 °C
• PSA: 125.68000
• Density: 1.27 g/cm³
• LogP: 1.84520
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 480.27231823
• Heavy Atom Count: 34
• Complexity: 811

Purity/Quality:

≥98% ^*data from raw suppliers

Neoandrographolide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCCC2(C1CCC(=C)C2CCC3=CCOC3=O)C)COC4C(C(C(C(O4)CO)O)O)O
• Isomeric SMILES: C[C@]1(CCC[C@@]2([C@@H]1CCC(=C)[C@H]2CCC3=CCOC3=O)C)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• Description: Andrographic plants are derived from the aerial parts of Andrographis paniculata (Burm.f.) Nees and known by various vernacular names such as “chunlianqiuliu,” “yijianxi,” “lanhelian,” “kudancao,” “jinxiangcao,” “jinergou,” “India grass,” and “bitter grass.” Andrographis paniculata is planted in South and Southeast Asia, India, and Australia. This herb is also cultivated in Fujian, Guangdong, Hainan, Guangxi, Yunnan, Jiangsu, and Shaanxi provinces in China. Andrographis paniculata has been used to treat colds, sore throat, mouth sores, cough, diarrhea dysentery, and so on. Andrographis paniculata contains diterpene lactone compounds, and they have anti-inflammatory and antimicrobial activities. The main active ingredients include andrographolide, neoandrographolide, deoxy andrographolide, dehydrated andrographolide, and so on. Andrographis paniculata has been included by US Pharmacopeia.
• Physical properties: Appearance: Neoandrographolide is a colorless column crystal that has been isolated from the stem and leaves of Andrographis paniculata. Melting point: 167– 168?°C. Specific optical rotation: ?48°(pyridine); ?45°(c?=?1, absolute ethanol). Solubility: Soluble in methanol, ethanol, acetone, and pyridine and slightly soluble in chloroform and water but insoluble in ether and petroleum ether.
• Uses: Neoandrographolide is one of the principle diterpenoids isolated from A. paniculata, a well-recognized medicinal plant in Asia.
• Indications: Neoandrographolide is available in the Pharmacopoeia of the People’s Republic of China (1977).Neoandrographolide and andrographolide are the main active ingredients of a variety of pharmaceutical preparations containing the Andrographis herb, such as andrographolide capsules, andrographolide tablets, Andrographis injection, potassium dehydroandrographolide succinate injection, Andrographis tablets, Xiaoyan Lidan tablets, and Fufang chuan xin lian tablets. These drugs are mainly used for treating acute bacterial dysentery, acute gastroenteritis, upper respiratory tract infection, acute tonsillitis, pharyngitis, etc. In addition, they are also used to treat malignant hydatidiform mole and choriocarcinoma.
• Clinical Use: Neoandrographolide is one of the main active ingredients of the natural plant Andrographis paniculata. But there is no formulation of neoandrographolide. Andrographis injection has been clinically used, but it has several side effects.

Technology Process of Neoandrographolide

There total 1 articles about Neoandrographolide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

UDP-glucose (133-89-1) + 19-hydroxy-8(17),13-ent-labdadien-15->16 lactone (82209-74-3) → neoandrographolide (27215-14-1,31222-64-7)

Guidance literature:

With glucosyltransferase from Andrographis paniculata; In aq. buffer; at 30 ℃; for 12h; pH=7.4; Reagent/catalyst; Kinetics; Enzymatic reaction;

DOI:10.1021/acs.orglett.8b02146

Reference yield: 99.0%

neoandrographolide (27215-14-1,31222-64-7) → 13,14-dihydroneoandrographolide

Guidance literature:

With sodium tetrahydroborate; nickel dichloride; In methanol; at 0 - 1 ℃;

DOI:10.1080/14786419.2012.682999

Reference yield:

neoandrographolide (27215-14-1,31222-64-7) → neoandrographolide isoaglucone (21681-03-8)

Guidance literature:

With hydrogenchloride; In ethanol; water; at 100 ℃; for 4h;

upstream raw materials:

UDP-glucose

19-hydroxy-8(17),13-ent-labdadien-15->16 lactone

Downstream raw materials:

19-hydroxy-8(17),13-ent-labdadien-15->16 lactone

neoandrographolide isoaglucone

19-acetoxy-8(17),13-ent-labdadien-15->16 lactone