Alantolactone

Base Information

• Chemical Name: Alantolactone
• CAS No.: 546-43-0
• Molecular Formula: C15H20O2
• Molecular Weight: 232.323
• Hs Code.: 29322090
• European Community (EC) Number: 215-803-3,208-899-3
• NSC Number: 93131
• UNII: M7GSN5Q1M6
• DSSTox Substance ID: DTXSID90877864
• Nikkaji Number: J13.573I
• Wikipedia: Helenin
• Wikidata: Q21099633
• Metabolomics Workbench ID: 28291
• ChEMBL ID: CHEMBL136356
• Mol file: 546-43-0.mol

Synonyms:alantolactone;helenin

Chemical Property of Alantolactone

Chemical Property:

• Appearance/Colour: Crystalline powder
• Vapor Pressure: 0.00523mmHg at 25°C
• Melting Point: 78-79 °C
• Refractive Index: 1.534
• Boiling Point: 274.999 °C at 760 mmHg
• Flash Point: 111.463 °C
• PSA: 26.30000
• Density: 1.088 g/cm³
• LogP: 3.24060
• Storage Temp.: ?20°C
• Solubility.: DMSO: soluble15mg/mL (clear solution)
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 232.146329876
• Heavy Atom Count: 17
• Complexity: 421

Purity/Quality:

99% ^*data from raw suppliers

Alantolactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36-36/37-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCCC2(C1=CC3C(C2)OC(=O)C3=C)C
• Isomeric SMILES: C[C@H]1CCC[C@]2(C1=C[C@H]3[C@@H](C2)OC(=O)C3=C)C
• Description: The allergen eudesmanolide sesquiterpene lactone was isolated from elecampane (Inula helenium L.). With dehydrocostuslactone and costunolide, it is a component of the (sesquiterpene) lactone-mix, used to detect sensitization to Compositae.
• Uses: anthelmintic, antibacterial, antineoplastic Alantolactone is sesquiterpene lactone that possesses anti-inflammatory property. Alantolactone have been studied to be developed as a novel agent against human liver cancer. Alantolactone has been used:in cell viability assayto examine the percentage of multicentrosomal mitosis in low and high passage human embryonic stem cells (hESC)in assessment of degranulation

Technology Process of Alantolactone

There total 11 articles about Alantolactone 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:

→ alantolactone (546-43-0)

Guidance literature:

DOI:10.1016/0040-4020(77)80301-3

Reference yield:

2,3,3aβ,5,6,7,8,8a,9,9aβ-decahydro-5β,8aβ-dimethyl-2-oxonaphtho<2,3-b>furan-3-carboxylic acid methyl ester (2658-80-2) → dl-7,8-epialantolactone (546-43-0,10067-20-6,69854-84-8,80367-94-8,97275-05-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / methanol; H₂O / Ambient temperature

2: 1.) diethylamine, 2.) sodium acetate, acetic acid / 1.) water

With sodium hydroxide; sodium acetate; acetic acid; diethylamine; In methanol; water;

DOI:10.1021/ja00527a046

Reference yield:

2bβ,2cβ,4,5,6,6a,7,7aβ-octahydro-6aβ-methyl-2-oxocyclopropanaphtho<2,3-b>furan-2a(2H)-carboxylic acid methyl ester (69841-27-6) → dl-7,8-epialantolactone (546-43-0,10067-20-6,69854-84-8,80367-94-8,97275-05-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / cuprous iodide / diethyl ether / 0.67 h / -20 - -5 °C

2: sodium hydroxide / methanol; H₂O / Ambient temperature

3: 1.) diethylamine, 2.) sodium acetate, acetic acid / 1.) water

With sodium hydroxide; copper(l) iodide; sodium acetate; acetic acid; diethylamine; In methanol; diethyl ether; water;

DOI:10.1021/ja00527a046

upstream raw materials:

formaldehyd

(3aS,5S,8aR,9aS)-5,8a-Dimethyl-2-oxo-2,3,3a,5,6,7,8,8a,9,9a-decahydro-naphtho[2,3-b]furan-3-carboxylic acid

2,3,3aβ,5,6,7,8,8a,9,9aβ-decahydro-5β,8aβ-dimethyl-2-oxonaphtho<2,3-b>furan-3-carboxylic acid methyl ester

2bβ,2cβ,4,5,6,6a,7,7aβ-octahydro-6aβ-methyl-2-oxocyclopropanaphtho<2,3-b>furan-2a(2H)-carboxylic acid methyl ester

Downstream raw materials:

13-(phenylthio)alantolactone

tetrahydroalantolactone

3,5,8a-trimethyl-3a,5,6,7,8,8a,9,9a-octahydro-3H-naphtho[2,3-b]furan-2-one

Refernces