Neohesperidin

Base Information

• Chemical Name: Neohesperidin
• CAS No.: 13241-33-3
• Molecular Formula: C₂₈H₃₄O₁₅
• Molecular Weight: 610.569
• Hs Code.: 29389090
• European Community (EC) Number: 236-216-9
• NSC Number: 31048
• Wikipedia: Neohesperidin
• Wikidata: Q104917305
• ChEMBL ID: CHEMBL4297019
• Mol file: 13241-33-3.mol

Synonyms:neohesperidin

Chemical Property of Neohesperidin

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 239-243 ºC
• Refractive Index: 1.695
• Boiling Point: 933.7 ºC at 760 mmHg
• PKA: 7.14±0.40(Predicted)
• Flash Point: 306.7 ºC
• PSA: 234.29000
• Density: 1.65 g/cm³
• LogP: -1.15660
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Pyridine (Slightly)
• Water Solubility.: 3.98mg/L at 20℃
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 7
• Exact Mass: 610.18977037
• Heavy Atom Count: 43
• Complexity: 940

Purity/Quality:

99% ^*data from raw suppliers

Neohesperidin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC(=C(C=C5)OC)O)O)CO)O)O)O)O)O
• Description: Neohesperidin is a flavonoid found in citrus fruit peel that has diverse biological activities. In vitro, it inhibits osteoclast differentiation, bone resorption, calcium oscillations, and activation of NF-κB and nuclear factor of activated T cells (NFAT) by receptor activator of NF-κB ligand (RANKL). In vivo, neohesperidin administration protects ovariectomized mice from bone loss. Neohesperidin acts as a hypolipidemic agent, reducing lipid accumulation in HepG2 cells and reversing hyperlipidemia in a mouse model of diet-induced obesity. In a mouse model of diabetes, neohesperidin increases glucose tolerance and decreases insulin resistance while simultaneously decreasing serum triglycerides and total cholesterol and inhibiting lipid accumulation in livers in vivo.
• Uses: Neohesperidin can be used in cosmetic products and as a sweetening agent in food & beverages, an antioxidant flavanone glycoside An antioxidant flavanone glycoside Neohesperidin exhibits lipid-regulating effects in vivo and in vitro. It is a main flavonoid in citrus byproducts (CBP) which possesses anti-oxidant activity.

Technology Process of Neohesperidin

There total 2 articles about Neohesperidin 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:

→ Neohesperidin (13241-33-3,61303-28-4,61303-29-5,61303-30-8,61347-97-5,61348-24-1,88294-38-6,139686-38-7)

Guidance literature:

Neohesperidosid (VII) 1. KOH/Isovanilin 2. Δ;

DOI:10.1021/jf60155a029

Reference yield:

→ 7-[(2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-chroman-4-one (13241-33-3,61303-28-4,61303-29-5,61303-30-8,61347-97-5,61348-24-1,88294-38-6,139686-38-7)

Guidance literature:

Rhamnopyranosylgalactopyranosyl-XII, Hesperetin;

Reference yield: 92.0%

neohesperidin (13241-33-3,61303-28-4,61303-29-5,61303-30-8,61347-97-5,61348-24-1,88294-38-6,139686-38-7) + vinyl laurate (2146-71-6) → 6''-O-lauroyl neohesperidin (502764-74-1)

Guidance literature:

With lipozyme TL IM from Thermomyces lanuginosus; In tert-Amyl alcohol; dimethyl sulfoxide; at 52 ℃; for 0.583333h; regioselective reaction; Flow reactor; Enzymatic reaction;

DOI:10.1016/j.carres.2017.11.008

Downstream raw materials:

4′-O-methylluteolin-7-O-rhamnoglucoside

2-O-α-L-rhamnopyranosyl-β-D-glucopyranose

hesperetin

neohesperidin