50781-91-4

Basic information

• Product Name: Methyl-7-hydroxyhept-5-ynoate
• Synonyms: Methyl-7-hydroxyhept-5-ynoate;7-Hydroxy-5-heptynoic Acid Methyl Ester;7-Bromoheptanoic Acid-d4 Methyl Ester
• CAS NO: 50781-91-4
• Molecular Formula: C₈H₁₂O₃
• Molecular Weight: 156.17908
• Mol File: 50781-91-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl-7-hydroxyhept-5-ynoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl-7-hydroxyhept-5-ynoate(50781-91-4)
• EPA Substance Registry System: Methyl-7-hydroxyhept-5-ynoate(50781-91-4)

Safety Data

• Hazardous Substances Data: 50781-91-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl-7-hydroxyhept-5-ynoate is used as an intermediate in the synthesis of Tianeptine for its psychostimulant, anti-ulcer, and anti-emetic properties. Methyl-7-hydroxyhept-5-ynoate plays a vital role in the production of Tianeptine, which is known to modulate the serotonin system in the brain, providing relief from various conditions such as depression, anxiety, and gastrointestinal issues.
Used in Antidepressant Applications:
As a component in the synthesis of Tianeptine, Methyl-7-hydroxyhept-5-ynoate contributes to the development of antidepressant medications. Tianeptine, the final product, is known to have a unique mechanism of action that involves the selective reuptake inhibition of serotonin, making it an effective treatment for depression and related disorders.
Used in Anti-ulcer Applications:
Methyl-7-hydroxyhept-5-ynoate is also used in the development of anti-ulcer medications. Tianeptine, synthesized using this intermediate, has been shown to exhibit anti-ulcer properties, providing relief from gastrointestinal ulcers and promoting healing in the stomach lining.
Used in Anti-emetic Applications:
In addition to its antidepressant and anti-ulcer properties, Methyl-7-hydroxyhept-5-ynoate is utilized in the synthesis of anti-emetic medications. Tianeptine, the final product, has been found to be effective in managing nausea and vomiting, making it a valuable asset in the treatment of various conditions that cause these symptoms, such as chemotherapy-induced nausea and motion sickness.

Upstream product

• 67-56-1 methanol 
• 34506-49-5 7-(tetrahydro-2'H-pyran-2'-yloxy)hept-5-ynoic acid 
• 50-00-0 formaldehyd 
• 82709-37-3 1,1,1-trimethoxy-5-hexyne 
• 34506-48-4 6-<(tetrahydropyranyl)oxy>-4-hexynenitrile 
• 110942-95-5 8-hydroxy-5-heptynoic acid, trimethyl orthoester 
• 50781-90-3 methyl 7-(tetrahydro-2'H-pyran-2'-yloxy)hept-5-ynoate 
• 110942-94-4 2-(7,7,7-Trimethoxy-hept-2-ynyloxy)-tetrahydro-pyran 
• 74723-68-5 7-chloro-1-(2H-tetrahydropyran-2-yloxy)-2-heptyne 
• 887110-61-4 7-acetoxy-hept-5-ynoic acid 
• 41300-59-8 7-Hydroxy-5-heptynoic Acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 53293-00-8 hex-5-ynoic acid 
• 73448-13-2 tert-butyldimethylsilyl hex-5-yn-1-yl ether 

Downstream Products

• 494222-00-3 (5Z)-7-((2R)-2-{(1E,3S)-3-hydroxy-4-[3-(methoxymethyl)phenyl]but-1-enyl}-5-oxopyrrolidin-1-yl)hept-5-enoic acid 
• 1369917-53-2 methyl (5Z)-7-[(2R)-2-{(1E)-4-[3-(methoxymethyl)phenyl]-3-oxo-1-buten-1-yl}-5-oxo-1-pyrrolidinyl]-5-heptenoate 
• 736141-49-4 tert-butyl-{(E)-1-[2-(3-chloro-benzo[b]thiophen-2-yl)-ethyl]-3-iodo-allyloxy}-dimethyl-silane 
• 659-86-9 propargyl iodide 
• 73958-00-6 methyl 10-formyl-5,6E-epoxy-7E,9E-decadienoate 
• 73957-99-0 (+/-)-methyl trans-5,6-epoxy-7-hydroxyheptanoate 
• 23453-26-1 (+/-)-prostaglandin E₂ methyl ester 
• 92134-15-1 11-O-(t-butyldimethylsilyl)-5,6-didehydro-15-O-(tetrahydropyran-2-yl)-7-thiobenzoyloxy-PGE₂ methyl ester 
• 96632-04-1 methyl (Z)-7-(p-tolylsulphonyloxy)hept-5-enoate 
• 315220-65-6 (Z)-7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-6-oxo-cyclohexyl}-hept-5-enoic acid methyl ester 
• 315220-61-2 7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-6-oxo-cyclohexyl}-hept-5-ynoic acid methyl ester 
• 315220-90-7 7-[(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((E)-oct-1-enyl)-6-oxo-cyclohexyl]-hept-5-ynoic acid methyl ester 
• 315221-01-3 (Z)-7-[(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((E)-oct-1-enyl)-6-oxo-cyclohexyl]-hept-5-enoic acid methyl ester 
• 315220-98-5 7-[(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-oxo-2-((E)-3-phenyl-propenyl)-cyclohexyl]-hept-5-ynoic acid methyl ester 

Relevant articles and documents

A Selective Synthesis of a Mixture of 15-Epimers of (+/-)-11-Deoxyprostaglandin E2 Methyl Ester

A highly regio- and stereoselective procedure for allylation of 3-alkenyl-substituted 1-cyclopentenolates involving the use of readily obtainable and thermally stable allylic acetates, BEt3 (2 equiv), and Pd(PPh3)4 (2 mol percent) was applied to the synthesis of a ca. 50:50 diastereomeric mixture of 11-deoxyprostaglandin E2 methyl ester (1a) and its 15-epimer (1b) as well as -2-(6'-methoxycarbonyl-2'-hexenyl)-3-ethenylcyclopentanone (5).The isolation yield of the allylated intermediate 8 for 1 was 74percent, and that of 5 was 66percent.Conversion of 8 into 1 wasachieved in 89percent yield.Apart from the fact that 8 was a ca. 50:50 diastereomeric mixture, the overall purities of the crude products, i.e., 5 and 8, were ca. 85-90percent.The major byproducts, which presumably were the products of γ-allylation, accounted for 5-10percent of the entire products.The regioselectivity with respect to cyclopentenone in each case was estimated to be nearly 100percent, and the overall stereoselectivity in each case was estimated to be ca. 95percent.

Synthesis of cyclooxygenase metabolites of 8,9-epoxyeicosatrienoic acid (EET): 11- and 15-hydroxy 8,9-EETs

COX metabolites of 8,9-EET, previously observed as potent mitogenic lipid mediators, were synthesized for the first time by using two synthetic approaches. These synthetic materials allow for structural confirmation of COX metabolites of 8,9-EET and furth

Methods of treating soft tissue defects

The specification discloses compositions and methods for treating a soft tissue defect of an individual.

Discovery of an 8-aza-5-thiaProstaglandin E1 analog as a highly selective EP4 receptor agonist

For the purpose of discovering an orally available EP4 subtype-selective agonist, a series of 8-aza prostaglandin E1 (PGE1) analogs were synthesized and evaluated for their affinity for PGE2 receptor subtypes. Additionally

2,3,4-Substituted cyclopentanones as therapeutic agents

Disclosed herein are compounds comprising or a pharmaceutically acceptable salt or a prodrug thereof, wherein a dashed line represents the presence or absence of a bond; Y is a carboxylic acid, sulfonic acid, or phosphonic acid functional group; or an amide or ester thereof comprising from 0 to 12 carbon atoms; or Y is hydroxymethyl or an ether thereof comprising from 0 to 12 carbon atoms; or Y is a tetrazolyl functional group; A is —(CH2)6—, cis —CH2—CH═CH—(CH2)3—, or —CH2—C≡C—(CH2)3— wherein 1 or 2 carbons may be substituted with S or O; B is hydrogen, C1-6 hydrocarbyl, CN, CO2H, or —(CH2)mX(CH2)pH, wherein m is at least 1 and the sum of m and p is from 1 to 5; X is S or O; J is H, CH3, or CF3; D is a covalent bond, CH2, O, or S; and E is an aromatic heterobicyclic ring system which may have substituents comprising up to 6 non-hydrogen atoms each. Methods, compositions, and medicaments related thereto are also disclosed.

A simplified synthesis of the diastereomers of Levuglandin E2

We report a synthesis of Levuglandin E2, as a mixture of easily separable diastereomers (15-E2-isoketals). The key feature is the protection of its reactive aldehyde as dimethyl acetal, which is introduced with 2,2-dimethoxyethanal and removed in minutes with Montmorillonite K-10. The synthesis could be modified to the preparation of 15-E2-isoketals with stable isotopes or with radiolabels. Copyright Taylor & Francis, Inc.

10,10-DIALKYL PROSTANOIC ACID DERIVATIVES AS AGENTS FOR LOWERING INTRAOCULAR PRESSURE

The present invention provides a method of treating ocular hypertension or glaucoma which comprises administering to an animal having ocular hypertension or glaucoma therapeutically effective amount of a compound represented by the general formula I; wherein the dashed line indicates the presence or absence of a bond, the hatched wedge indicates the α (down) configuration, and the solid triangle indicates the β (up) configuration; B is a single, double, or triple covalent bond; n is 0-6; X is CH2, S or O; Y is any pharmaceutically acceptable salt of CO2H, or CO2R, CONR2, NHCH2CH2OH, N(CH2CH2OH)2, CH2OR, P(O)(OR)2, CONRSO2R, SONR2, or R is H, C1-6 alkyl or C2-6 alkenyl; R2 and R3 are C1-6 linear alkyl which may be the same or different, and may be bonded to each other such that they form a ring incorporating the carbon to which they are commonly attached; R4 is hydrogen, R, C(═O)R, or any group that is easily removed under physiological conditions such that R4 is effectively hydrogen; R5 is hydrogen or R; R6 is iv) hydrogen; v) a linear or branched hydrocarbon containing between 1 and 8 carbon atoms, which may contain one or more double or triple bonds, or oxygen or halogen derivatives of said hydrocarbon, wherein 1-3 carbon or hydrogen atoms may be substituted by O or a halogen; or vi) aryloxy, heteroaryloxy, C3-8 cycloalkyloxy, C3-8 cycloalkyl, C6-10 aryl or C3-10 heteroaryl, wherein one or more carbons is substituted with N, O, or S; and which may contain one or more substituents selected from the group consisting of halogen, trihalomethyl, cyano, nitro, amino, hydroxy, C6-10 aryl, C3-10 heteroaryl, aryloxy, heteroaryloxy, C1-6 alkyl, OR, SR, and SO2R. Some of the compounds of the present invention and some of their methods of preparation are also novel an nonobvious.

Analysis of oxidized glycerophosphocholine lipids using electrospray ionization mass spectrometry and microderivatization techniques

Oxidized low-density lipoprotein (LDL) is thought to play an important role in atherogenesis and cardiovascular disease in humans. Oxidized LDL is a complex mixture of many oxidized species, including numerous oxidized glycerophospholipids. Electrospray i

Process for the preparation of cyclopentanoids and novel intermediates produced thereby

Cyclopentanoids (I) of the formula: STR1 including stereoisomers are described along with a process for the preparation of I. In particular the preparation of prostanoids of the formula: STR2 wherein R1 is a alkyl group containing 1 to 8 carbon atoms and R2 CO2 R3 is an alkenyl ester group, R2 contains 2 to 6 carbon atoms and R3 is a lower alkyl group containing 1 to 6 carbon atoms is described. A particular prostaglandin prepared by the process is PGE2. The prostanoids have been demonstrated to have pharmacological activity in animals and humans. Novel intermediates of (I) are also described.

The Efficient Synthesis of Two Prostaglandin Intermediates

This paper presents new synthetic routes for methyl cis-7-iodo-5-heptenoate (7) and 3-hydroxycyclopent-2-enone (15a), useful intermediates in the synthesis of prostanoids.