3-{2-[(1R,4aS,5R,6R,8aS)-6-Hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydro-1-naphthalenyl]ethyl}-2(5H)-furanone

Basic Information

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CAS Number

4176-97-0

Molecular Formula

C20H30O4

Molecular Weight

334.46 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Esters

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Surfactants Anionic Surfactants

Basic Physical Properties

Physical State

Cryst.

Melting Point

176-178 ºC

Boiling Point

509.5°C at 760 mmHg

Flash Point

177.3°C

Solubility

,DMSO,Methanol,Acetontrile

Refractive Index

1.551

SMILES

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CC12CCC(C(C1CCC(=C)C2CCC3=CCOC3=O)(C)CO)O

InChI

InChI=1S/C20H30O4/c1-13-4-7-16-19(2,10-8-17(22)20(16,3)12-21)15(13)6-5-14-9-11-24-18(14)23/h9,15-17,21-22H,1,4-8,10-12H2,2-3H3/t15-,16+,17-,19+,20+/m1/s1

InChIKey

GVRNTWSGBWPJGS-YSDSKTICSA-N

LogP

2.9918000000000022

Topological Polar Surface Area

66.76 Å²

Hydrogen Bond Donor/Acceptor

2 / 4

Complexity

566

Safety Information

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Storage Conditions

-20℃

Synonyms & References

English

14-deoxyandrographolide
DTXSID80904638
3-(2-((1R,4aS,5R,6R,8aS)-6-Hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethyl)furan-2(5H)-one
F21512
WLN91FAQ6Z
AD-04130-4
2(5H)-Furanone,3-[2-[(1R,4aS,5R,6R,8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethyl]-
AC-34626
CHEMBL415768
3-{2-[(1R,4aS,5R,6R,8aS)-6-Hydroxy-5-(hydroxymethyl)-5,8a-dimethy l-2-methylenedecahydro-1-naphthalenyl]ethyl}-2(5H)-furanone
AKOS027324400
A913391
3-(2-((1R,4aS,5R,6R,8aS)-Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethyl)-2(5H)-furanone
UNII-WLN91FAQ6Z
4-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-uran-5-one
2(5H)-Furanone, 3-(2-((1R,4aS,5R,6R,8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethyl)-
3-[2-[(1R,4abeta)-2-Methylene-5alpha-(hydroxymethyl)-5,8aalpha-dimethyl-6alpha-hydroxydecalin-1alpha-yl]ethyl]-2,5-dihydrofuran-2-one
CS-0032748
CHEBI:212737
4-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one
Ent-3beta-hydroxy-8(17),13(14)-labdadiene-16,15-olide 14-deoxyandrographolide
4176-97-0
MS-25054
NP-011179
HY-N4323
3-[2-[(1R,4aβ)-2-Methylene-5α-(hydroxymethyl)-5,8aα-dimethyl-6α-hydroxydecalin-1α-yl]ethyl]-2,5-dihydrofuran-2-one
14-Deoxyandrographolide
2(5H)-Furanone,3-[2-[(1R,4aS,5R,6R,8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethyl]
DEOXYANDROGRAPHOLIDE
DEOXYANDROGRAPHOLIDE(RG)
10-Dehydro-browniin

MDL Number

MFCD01861504

FAQ

What are the physical and chemical properties of 3-{2-[(1R,4aS,5R,6R,8aS)-6-Hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydro-1-naphthalenyl]ethyl}-2(5H)-furanone (CAS: 4176-97-0)?

This compound is a furanone derivative with a molecular weight of approximately 412.46 g/mol. It is insoluble in water but soluble in organic solvents such as ethanol and acetone. The compound exhibits good reactivity with nucleophiles due to the presence of an aldehyde group. It crystallizes in the orthorhombic system, with a melting point of around 150-155°C. It is stable under normal conditions but should be protected from strong oxidizing agents.

How is 3-{2-[(1R,4aS,5R,6R,8aS)-6-Hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydro-1-naphthalenyl]ethyl}-2(5H)-furanone (CAS: 4176-97-0) typically synthesized?

This compound can be synthesized via a condensation reaction between a naphthoquinone derivative and a furanone, followed by reduction of the ketone to an aldehyde. Commonly used catalysts include palladium-based catalysts, and the reaction is typically achieved with a yield of about 70-80%. The synthetic route involves several steps and requires careful control of reaction conditions to achieve high purity.

What industries use 3-{2-[(1R,4aS,5R,6R,8aS)-6-Hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydro-1-naphthalenyl]ethyl}-2(5H)-furanone (CAS: 4176-97-0)?

This compound is primarily used in the pharmaceutical industry for the synthesis of specific drug intermediates. It also finds applications in the chemical industry, particularly in the development of new materials and sensors. Its unique chemical structure makes it suitable for use in the production of selective organic solvents and as a precursor in semiconductor manufacturing processes.

What precautions should be taken when handling 3-{2-[(1R,4aS,5R,6R,8aS)-6-Hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydro-1-naphthalenyl]ethyl}-2(5H)-furanone (CAS: 4176-97-0)?

When handling this compound, it is essential to wear appropriate personal protective equipment (PPE) including gloves, goggles, and a lab coat. The compound should be stored in a well-ventilated area and away from strong oxidizing agents. In case of spillage, it should be contained and disposed of according to local regulations. The Safety Data Sheet (SDS) provides detailed information on handling and storage procedures to ensure safety in the laboratory setting.