Gardenoside

Base Information

• Chemical Name: Gardenoside
• CAS No.: 24512-62-7
• Molecular Formula: C17H24 O11
• Molecular Weight: 404.371
• Hs Code.: 2938909090
• UNII: INE79XNR2C
• Nikkaji Number: J16.694D
• Wikidata: Q104885561
• ChEMBL ID: CHEMBL1079679
• Mol file: 24512-62-7.mol

Synonyms:gardenoside;gardenoside, 1S(1alpha,4alplha,7beta,7alpha)

Chemical Property of Gardenoside

Chemical Property:

• Appearance/Colour: Powder.
• Vapor Pressure: 5.53E-21mmHg at 25°C
• Melting Point: 118-120ºC
• Boiling Point: 672.8 °C at 760 mmHg
• PKA: 12.28±0.60(Predicted)
• Flash Point: 242.1 °C
• PSA: 175.37000
• Density: 1.61 g/cm³
• LogP: -3.25830
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 6
• Exact Mass: 404.13186158
• Heavy Atom Count: 28
• Complexity: 649

Purity/Quality:

10%-98% ^*data from raw suppliers

Gardenoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=COC(C2C1C=CC2(CO)O)OC3C(C(C(C(O3)CO)O)O)O
• Isomeric SMILES: COC(=O)C1=CO[C@H]([C@H]2[C@@H]1C=C[C@]2(CO)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• Uses: Gardenoside is a plant extract used in traditional chinese medicine as a component of an anti-viral medicine. Component of Zhi-zi-chi decoction used as an anti-depression medication.

Technology Process of Gardenoside

There total 10 articles about Gardenoside 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:

10-dehydrogardenoside (82345-51-5) → gardenoside (24512-62-7)

Guidance literature:

With sodium tetrahydroborate; In ethanol; for 1h; Ambient temperature;

Reference yield:

(RS)-(+/-)-<10-(3)H>-10-hydroxycitronellol → tarennoside (61081-59-2) + gardenoside (24512-62-7,54712-59-3)

Guidance literature:

for 240h; Product distribution; Mechanism; Gardenia jasminoides f. grandiflora cell cultures; products labelled with ⁽³⁾H;

Reference yield:

<10-(3)H>-10-hydroxygeraniol (69252-86-4) → tarennoside (61081-59-2) + gardenoside (24512-62-7,54712-59-3)

Guidance literature:

for 240h; Product distribution; Mechanism; Gardenia jasminoides f. grandiflora cell cultures; products labelled with ⁽³⁾H;

upstream raw materials:

10-dehydrogardenoside

<4-(13)C>-10-hydroxygeraniol

(S)-(-)-<9-¹³C>-10-hydroxycitronellol

<2-¹³C>-9,10-dihydroxygeraniol

Downstream raw materials:

randioside

Refernces

• 1、 Abe, Fumiko,Mori, Tomojiro,Yamauchi, Tatsuo. "Iridoids of Apocynaceae. III. Minor Iridoids from Allamanda neriifolia". . p. 2947 - 2956. Retrieved 2007/10/02.