Ophiobolin A | CAS No. 4611-05-6

Ophiobolin A

Basic Information

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CAS Number

4611-05-6

Molecular Formula

C25H36O4

Molecular Weight

400.56 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Aldehydes

Basic Chemical Raw Materials Organic Chemicals Ketones

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

Polymers and Plastics Thermoplastics Polyolefins

Laboratory Chemicals Research Chemicals Biochemical Reagents

Basic Physical Properties

Melting Point

182°C

Boiling Point

443.19°C (rough estimate)

Refractive Index

1.4460 (estimate)

SMILES

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CC1CC(OC12CCC3(C2CC=C(C4C(C3)C(CC4=O)(C)O)C=O)C)C=C(C)C

InChI

InChI=1S/C25H36O4/c1-15(2)10-18-11-16(3)25(29-18)9-8-23(4)12-19-22(20(27)13-24(19,5)28)17(14-26)6-7-21(23)25/h6,10,14,16,18-19,21-22,28H,7-9,11-13H2,1-5H3/b17-6-/t16-,18-,19-,21+,22+,23+,24+,25-/m0/s1

InChIKey

MWYYLZRWWNBROW-BDZRSQQBSA-N

LogP

4.408000000000004

Topological Polar Surface Area

63.6 Å²

Hydrogen Bond Donor/Acceptor

1 / 4

Complexity

778

Synonyms & References

English

ophiobolin a
(18R)-14,18-Epoxy-3-hydroxy-5-oxoophiobola-7,19-dien-25-al
(18R)-3-Hydroxy-5-oxo-14,18-epoxyophiobola-7,19-diene-25-al
(7E,18R)-3-hydroxy-5-oxo-14,18-epoxyophiobola-7,19-dien-25-al
18-epoxy-3-hydroxy-5-oxo-19-dien-25-a(18r)-ophiobola-14
cochliobolin
COCHLIOBOLIN A
ophiobolin
Ophiobolin,Helminthosporium sp.
orphiobolin A
(2′S,3′S,3aR,5′R,6aS,9R,9aS,10aR)-1,3a,4,4′,5′,6a,7,8,9,9a,10,10a-Dodecahydro-9-hydroxy-3′,9,10a-trimethyl-5′-spiro[dicyclopenta[a,d]cyclooctene-3(2H),2′(3′H)-furan]-6-carboxaldehyde
CHEBI:7777
HY-N6781
(18R)-3-hydroxy-5-oxo-14,18-epoxyophiobola-7,19-dien-25-al
Ophiobolin
G16870
Spiro(dicyclopenta(a,d)cyclooctene-3(2H),2'(3'H)-furan)-6-carboxaldehyde, 1,3a,4,4',5',6a,7,8,9a,10,10a-dodecahydro-9-hydroxy-3',9,10a-trimethyl-5'-(2-methyl-1-propenyl)-7-oxo-, (2'S,3'S,3aR,5'R,6aS,9R,9aS,10aR)-
Ophiobolin A, >=95% (HPLC)
4611-05-6
(1'R,2S,3S,3'S,4'R,5R,7'S,8'E,11'R)-4'-hydroxy-1',3,4'-trimethyl-5-(2-methylprop-1-enyl)-6'-oxospiro[oxolane-2,12'-tricyclo[9.3.0.03,7]tetradec-8-ene]-8'-carbaldehyde
(2'S,3'S,3aR,5'R,6aS,9R,9aS,10aR)-1,3a,4,4',5',6a,7,8,9,9a,10,10a- dodecahydro-9-hydroxy-3',9,10a-trimethyl-5'-(2-methylpropen-1-yl)-7- oxospiro[dicyclopenta[a,d]cyclooctene-3(2H),2'(3'H)-furan]-6-carbaldehyde
CS-0093830
Q27107581
Ophiobolin A
CHEMBL522808
(18R)-14,18-epoxy-3-hydroxy-5-oxoophiobola-7,19-dien-25-al
NSC 114340
Ophiobola-7,19-dien-25-al, 14,18-epoxy-3-hydroxy-5-oxo-, (18R)-
LMPR0105050001
C09145
SCHEMBL1959293

MDL Number

MFCD00058400

FAQ

What are the physical and chemical properties of Ophiobolin A (CAS: 4611-05-6)?

Ophiobolin A (CAS: 4611-05-6) is a cyclic depsipeptide with a molecular weight of approximately 449.37 g/mol. It is poorly soluble in water but soluble in organic solvents like methanol and acetone. Ophiobolin A is relatively stable under normal conditions but shows increased reactivity towards acidic conditions. It crystallizes in the form of colorless needles at room temperature.

How is Ophiobolin A (CAS: 4611-05-6) typically synthesized?

Ophiobolin A (CAS: 4611-05-6) is typically synthesized through solid-phase peptide synthesis (SPPS) followed by deprotection and coupling steps. Commonly used catalysts include t-Boc and Fmoc protecting groups. The synthetic route involves multiple steps of amino acid coupling, deprotection, and purification, yielding a product with high selectivity and yield.

What industries use Ophiobolin A (CAS: 4611-05-6)?

Ophiobolin A (CAS: 4611-05-6) is primarily used in the pharmaceutical industry due to its antifungal and antibiotic properties. It is also of interest in the agricultural sector for developing fungicides. Additionally, it has potential applications in the sensor technology and material science industries for its unique chemical and physical properties.

What precautions should be taken when handling Ophiobolin A (CAS: 4611-05-6)?

When handling Ophiobolin A (CAS: 4611-05-6), it is important to wear appropriate personal protective equipment (PPE) including gloves, safety goggles, and a lab coat. Work should be conducted in a well-ventilated area or a fume hood to minimize inhalation risks. Spills should be immediately cleaned up using appropriate absorbent materials, and the area should be thoroughly washed down. Always refer to the Safety Data Sheet (SDS) for detailed handling and disposal instructions.