(1R)-1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydro-2-naphthalenyl)-4-methyl-3-penten-1-yl 3-methyl-2-butenoate

Basic Information

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CAS Number

24502-79-2

Molecular Formula

C21H22O6

Molecular Weight

370.4 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Ketones

Basic Chemical Raw Materials Organic Chemicals Esters

Basic Chemical Raw Materials Organic Chemicals Ethers

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Basic Physical Properties

Physical State

Powder

Melting Point

103.0 to 105.0 deg-C

Boiling Point

587.3°Cat760mmHg

Flash Point

206.4°C

Solubility

N/A

Refractive Index

1.618

SMILES

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C/C(C)=C\C[C@H](C(C(C1=C2C(O)=CC=C1O)=O)=CC2=O)OC(/C=C(C)\C)=O

InChI

InChI=1S/C21H22O6/c1-11(2)5-8-17(27-18(25)9-12(3)4)13-10-16(24)19-14(22)6-7-15(23)20(19)21(13)26/h5-7,9-10,17,22-23H,8H2,1-4H3/t17-/m1/s1

InChIKey

BATBOVZTQBLKIL-QGZVFWFLSA-N

LogP

3.637500000000003

Topological Polar Surface Area

100.9 Å²

Hydrogen Bond Donor/Acceptor

2 / 6

Complexity

706

Safety Information

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Storage Conditions

2-8℃

Synonyms & References

English

β,β-Dimethylacrylshikonin
2-Butenoic acid,3-methyl-,(1R)-1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalenyl)-4-methyl-3-penten-1-ylester
(beta,beta-Dimethylacryl)shikonin
(β,β-DIMETHYLACRYL)SHIKONIN
2-Butenoic acid,3-methyl-,(1R)-1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalenyl)-4-methyl...
b,b-Dimethylacrylshikonin
beta,beta-Dimethylacrylshikonin
Beta,beta-DimethylacrylAlkannin
Dimethylacrylshikonin
dmask
Isoarnebin I
Senecioylshikonin
5,8-Dihydroxy-2-[1-(β,β-dimethylacryloyloxy)-4-methyl-3-pentenyl]-1,4-naphthalenedione
Shikonin beta,beta-dimethylacrylate
3-Methyl-2-butenoic acid (1R)-1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalenyl)-4-methyl-3-penten-1-yl ester
Beta,beta- Dimethylacrylshikonin
(,-DIMETHYLACRYL)SHIKONIN
[1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-methylbut-2-enoate
[(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-methylbut-2-enoate
2-Butenoic acid, 3-methyl-, (1R)-1-(1,4-dihydro-5,8-dihydroxy-1,4-dio

MDL Number

MFCD00143687

Customs Code

2916129000

FAQ

What are the physical and chemical properties of (1R)-1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydro-2-naphthalenyl)-4-methyl-3-penten-1-yl 3-methyl-2-butenoate (CAS: 24502-79-2)?

(1R)-1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydro-2-naphthalenyl)-4-methyl-3-penten-1-yl 3-methyl-2-butenoate is a crystalline compound with a molecular weight of approximately 448.39 g/mol. It has a low solubility in water but is soluble in organic solvents such as ethanol and acetone. The compound is reactive, particularly towards nucleophilic substitution and addition reactions. It is stable under normal laboratory conditions, although it should be stored in a cool, dry place to prevent degradation.

How is (1R)-1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydro-2-naphthalenyl)-4-methyl-3-penten-1-yl 3-methyl-2-butenoate (CAS: 24502-79-2) typically synthesized?

(1R)-1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydro-2-naphthalenyl)-4-methyl-3-penten-1-yl 3-methyl-2-butenoate is synthesized via a multistep process involving the condensation of 4-methyl-3-penten-1-yl 3-methyl-2-butenoyl chloride with 5,8-dihydroxy-1,4-dioxo-1,4-dihydro-2-naphthalenyl 1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydro-2-naphthalenyl)ethanone, using a suitable base as a catalyst. The yield is typically around 70%, and the reaction is carried out under anhydrous conditions to enhance selectivity and yield.

What industries use (1R)-1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydro-2-naphthalenyl)-4-methyl-3-penten-1-yl 3-methyl-2-butenoate (CAS: 24502-79-2)?

(1R)-1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydro-2-naphthalenyl)-4-methyl-3-penten-1-yl 3-methyl-2-butenoate finds applications in the pharmaceutical industry for its potential in drug synthesis, particularly in the development of new anticancer drugs. It is also used in the polymer industry as a monomer for the development of special polymers with unique properties. Additionally, it has potential uses in sensors and semiconductor manufacturing due to its chemical reactivity and structural complexity.

What precautions should be taken when handling (1R)-1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydro-2-naphthalenyl)-4-methyl-3-penten-1-yl 3-methyl-2-butenoate (CAS: 24502-79-2)?

When handling (1R)-1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydro-2-naphthalenyl)-4-methyl-3-penten-1-yl 3-methyl-2-butenoate, appropriate personal protective equipment (PPE) should be worn, including gloves, goggles, and a lab coat. The compound should be handled in a well-ventilated area or a fume hood to prevent inhalation. In case of a spill, it should be handled using appropriate spill cleanup procedures, and the area should be well-ventilated. For detailed safety information, refer to the Material Safety Data Sheet (MSDS) or Safety Data Sheet (SDS).