(2R,3S,4S,4aS,10bR)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c][2]benzopyran-6-one

Base Information

• Chemical Name: (2R,3S,4S,4aS,10bR)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c][2]benzopyran-6-one
• CAS No.: 477-90-7
• Molecular Formula: C14H16O9
• Molecular Weight: 328.276
• Hs Code.: 29329990
• NSC Number: 757796
• Wikidata: Q27167076
• Mol file: 477-90-7.mol

Synonyms:Spectrum_001129;SpecPlus_000565;Spectrum2_000600;Spectrum3_000623;Spectrum4_001880;Spectrum5_000480;BSPBio_002186;KBioGR_002383;KBioSS_001609;DivK1c_006661;SPECTRUM1500819;SPBio_000480;SCHEMBL17131822;CHEBI:95241;KBio1_001605;KBio2_001609;KBio2_004177;KBio2_006745;KBio3_001686;Pharmakon1600-01500819;CCG-38520;NSC757796;AKOS015909329;SDCCGMLS-0066671.P001;NCGC00178774-01;PD063300;SBI-0052329.P002;AB00052838_02;BRD-K18550767-001-02-8;BRD-K18550767-002-01-8;Q27167076;(2R,3S,4S,4aS,10bR)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c][2]benzopyran-6-one

Chemical Property of (2R,3S,4S,4aS,10bR)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c][2]benzopyran-6-one

Chemical Property:

• Appearance/Colour: the loose white needle crystal powder or crystalline
• Vapor Pressure: 2.92E-18mmHg at 25°C
• Melting Point: 237-240 °C
• Refractive Index: 1.655
• Boiling Point: 658.9 °C at 760 mmHg
• PKA: 8.26±0.70(Predicted)
• Flash Point: 250.7 °C
• PSA: 145.91000
• Density: 1.639 g/cm³
• LogP: -1.20060
• Storage Temp.: ?20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 2
• Exact Mass: 328.07943208
• Heavy Atom Count: 23
• Complexity: 458

Purity/Quality:

99% ^*data from raw suppliers

Bergenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1O)C3C(C(C(C(O3)CO)O)O)OC2=O)O
• Isomeric SMILES: COC1=C(C=C2C(=C1O)[C@@H]3[C@H]([C@H]([C@@H]([C@H](O3)CO)O)O)OC2=O)O
• Description: The plant resources of bergenin are rich, mainly from Rock cabbage (Bergenia purpurascens) and thick leafy rock cabbage (Astilbe macroflora) from Saxifragaceae and the roots, stems, and leaves of bai liang jin (Ardisia crispa) from Ardisia japonica (Thunb.) Blume. In Chinese medicine Rock cabbage (Bergenia purpurascens) is the common folk medicine, with nourishing, stanching bleeding, relieving a cough, and other effects. Its earliest record is contained in the classified herbal in Qing Dynasty .There are ten kinds of Rock cabbage (Bergenia purpurascens) in Asia, mainly growing in East Asia, north of South Asia, and southeastern Central Asia. There are seven species (including three endemic species) in China, mainly distributed in Shaanxi (Qinling), Xinjiang, Sichuan, Yunnan, and Tibet .
• Physical properties: Appearance: white, loose needle-like crystal or crystalline powder with light odor and bitter taste and discolored when encountered with light or heat. Solubility: dissolved in methanol and slightly soluble in water or ethanol. Melting point: 232– 240?°C. Specific optical rotation: ?38° to ?45°.
• Uses: A herbal remedy with antioxidant, antimicrobial and antiinflammatory properties.
• Clinical Use: Bergenin was recorded in People’s Republic of China Pharmacopoeia as an antitussive expectorant, used for the treatment of chronic bronchitis, emphysema, bronchial asthma, and other respiratory diseases. Used alone, or in compound preparation, such as compound bergenin tablets, Qingjin syrup, Compound Hu ear tablets, Qingfei antitussive syrup, liver poison net particles, Kechuanping oral solution, and silicone lung oral solution, it is mainly used for the treatment of chronic bronchitis. Its efficacy was proven to be relatively stable and improved in the compound preparations after a wide range of clinical validation.

Technology Process of (2R,3S,4S,4aS,10bR)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c][2]benzopyran-6-one

There total 6 articles about (2R,3S,4S,4aS,10bR)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c][2]benzopyran-6-one 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: 48.9%

C24H24NO11Pol → C10H10NO3Pol + bergenin (477-90-7)

Guidance literature:

With sulfuric acid; In water; solid phase reaction;

DOI:10.1016/j.tetlet.2009.12.119

Reference yield:

bergenin-8-O-α-L-rhamnoside → L-Rhamnose (3615-41-6,478518-52-4) + bergenin (477-90-7)

Guidance literature:

With hydrogenchloride; water; at 100 ℃; for 3h; Reflux;

DOI:10.3987/COM-14-12969

Reference yield:

seco-bergenin-8-O-α-L-rhamnoside → L-Rhamnose (3615-41-6,478518-52-4) + bergenin (477-90-7)

Guidance literature:

With hydrogenchloride; water; at 100 ℃; for 3h; Reflux;

DOI:10.3987/COM-14-12969

upstream raw materials:

11-O-(3',4',5'-trihydroxygalloyl)bergenin

bergenin-4-O-gallate

mallotannin A

Refernces

• 1、 Luangruangrong, Kongsin,Sritularak, Boonchoo,Lipipun, Vimolmas,Likhitwitayawuid, Kittisak. "New gallic acid glycosides from mallotus plicatus". . p. 1237 - 1244. Retrieved 2014/05/20.
• 2、 Yoshida, Takashi,Seno, Kaoru,Takama, Yukiko,Okuda, Takuo. "BERGENIN DERIVAVTIVES FROM MALLOTUS JAPONICUS". . p. 1180 - 1182. Retrieved 2007/10/02.