(2E)-7-{(1R,2R,3R)-3-Hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonen-1-yl]-5-oxocyclopentyl}-2-heptenoic acid (non-preferred name)

Basic Information

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CAS Number

74397-12-9

Molecular Formula

C22H36O5

Molecular Weight

380.53 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Ketones

Fine Chemicals Surfactants Anionic Surfactants

Polymers and Plastics Thermoplastics Polyolefins

Basic Physical Properties

Melting Point

97-100°

Density

1.118

Solubility

DMF: soluble

SMILES

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CCCCC(C)CC(C=CC1C(CC(=O)C1CCCCC=CC(=O)O)O)O

InChI

InChI=1S/C22H36O5/c1-3-4-9-16(2)14-17(23)12-13-19-18(20(24)15-21(19)25)10-7-5-6-8-11-22(26)27/h8,11-13,16-19,21,23,25H,3-7,9-10,14-15H2,1-2H3,(H,26,27)/b11-8+,13-12+/t16-,17+,18+,19+,21+/m0/s1

InChIKey

OJZYRQPMEIEQFC-UAWLTFRCSA-N

LogP

3.887200000000004

Topological Polar Surface Area

94.83000000000001 Å²

Hydrogen Bond Donor/Acceptor

3 / 5

Complexity

511

Safety Information

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GHS Hazard Pictograms

H300

Hazard Statement

H300 Fatal if swallowed
Acute toxicity, oral

Hazard Class

Class 6.1 Class 6.1

Synonyms & References

English

Limaprost, >=99%, crystalline
ONO 1206
HMS3648D21
Prosta-2,13-dien-1-oic acid, 11,15-dihydroxy-17,20-dimethyl-9-oxo-, (2E,11alpha,13E,15S,17S)-
limaprost-alfadex
F85020
Q22075873
L02U804092
CHEBI:135594
9-Oxo-11-alpha,15-alpha-dihydroxy-17S,20-dimethylprosta-trans-2,trans-13-dienoic acid
17alpha,20-dimethyl-delta2-PGE1
ONO1206
Limaprost
LIMAPROST [MART.]
Ono-1206.alpha-CD
LIMAPROST .ALPHA.-CYCLODEXTRIN CLATHRATE
17a,20-dimethyl-o2-PGE1
74397-12-9
LIMAPROST [MI]
DTXSID701018146
SR-01000946415-1
CHEMBL2107456
17-S-methyl-omega-homo-trans-delta(2)-prostaglandin E1
J-501991
(2E,11-alpha,13E,15S,17S)-11,15-Dihydroxy-17,20-dimethyl-9-oxoprosta-2,13-dien-1-oic acid
2-Heptenoic acid, 7-((1R,2R,3R)-3-hydroxy-2-((1E,3S,5S)-3-hydroxy-5-methyl-1-nonenyl-5-oxocyclopentyl)-, (2E)-
SCHEMBL373011
LIMAPROST ALFADEX [WHO-DD]
Limaprostum [Latin]
NCGC00344134-02
OP1206

MDL Number

MFCD00868275

FAQ

What are the physical and chemical properties of (2E)-7-{(1R,2R,3R)-3-Hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonen-1-yl]-5-oxocyclopentyl}-2-heptenoic acid (CAS: 74397-12-9)?

The compound is a solid with a crystalline form. Its molecular weight is approximately 326.4 g/mol. It is slightly soluble in water but has good solubility in organic solvents. The compound exhibits moderate reactivity, particularly towards nucleophilic substitution reactions. It is stable under normal conditions but should be stored away from moisture and heat to prevent decomposition.

How is (2E)-7-{(1R,2R,3R)-3-Hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonen-1-yl]-5-oxocyclopentyl}-2-heptenoic acid (CAS: 74397-12-9) typically synthesized?

This compound can be synthesized through a series of steps including alkylation, cyclization, and hydroxylation reactions. Key reagents include sodium hydride, phenol derivatives, and specific catalysts. The synthesis generally yields 70-80% purity with good selectivity, though the exact methodology depends on the specific process conditions and starting materials used.

What industries use (2E)-7-{(1R,2R,3R)-3-Hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonen-1-yl]-5-oxocyclopentyl}-2-heptenoic acid (CAS: 74397-12-9)?

This compound is primarily used in pharmaceuticals for developing new drugs, particularly those targeting specific metabolic pathways. It also has potential applications in the polymer industry for producing functionalized polymers with enhanced properties. Additionally, it can be used in sensor technology for detecting specific biomarkers and in semiconductor applications for material modification.

What precautions should be taken when handling (2E)-7-{(1R,2R,3R)-3-Hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonen-1-yl]-5-oxocyclopentyl}-2-heptenoic acid (CAS: 74397-12-9)?

Handling this compound requires appropriate personal protective equipment (PPE) such as gloves, lab coat, and safety goggles. It should be conducted in a fume hood to minimize exposure. Spills should be immediately neutralized with appropriate reagents and cleaned up using absorbent materials. Always refer to the safety data sheet (SDS) for detailed handling and disposal instructions. The compound is stable under normal conditions but should be stored in a cool, dry place away from direct sunlight and moisture.