73836-78-9

Usage

Uses

1. Used in Pharmaceutical Research:
LTD4 is used as a pharmacological tool for studying the effects of leukotrienes on smooth muscle contraction, vascular permeability, and their role in asthma and allergic reactions. It helps researchers understand the underlying mechanisms of these conditions and develop targeted therapies.
2. Used in Drug Development:
LTD4 is employed in the development of drugs that target leukotriene receptors or their synthesis pathways. By understanding the interactions between LTD4 and its receptors, researchers can design drugs that modulate these interactions, potentially leading to more effective treatments for asthma and other leukotriene-mediated diseases.
3. Used in Diagnostic Applications:
LTD4 can be used as a diagnostic marker for assessing the severity of asthma and allergic reactions. By measuring the levels of LTD4 in biological samples, clinicians can gain insights into the patient's condition and tailor their treatment strategies accordingly.
4. Used in Toxicology Studies:
LTD4 is utilized in toxicology research to evaluate the potential effects of various substances on the respiratory and cardiovascular systems. By studying the interactions between LTD4 and these substances, researchers can identify potential toxicants and develop strategies to mitigate their harmful effects.
5. Used in Basic Research:
LTD4 serves as an important research tool in basic science, particularly in the fields of cell biology, immunology, and biochemistry. It helps researchers investigate the complex signaling pathways and cellular responses triggered by leukotrienes, contributing to a deeper understanding of their role in health and disease.

Biochem/physiol Actions

Slow reacting substance of anaphylaxis (SRS-A). Potent bronchoconstrictor and mediator of asthmatic and inflammatory processes. Increases cytosolic free Ca2+ in epithelial cells.

InChI:InChI=1/C25H40N2O6S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-22(21(28)15-14-17-23(29)30)34-19-20(26)25(33)27-18-24(31)32/h6-7,9-13,16,20-22,28H,2-5,8,14-15,17-19,26H2,1H3,(H,27,33)(H,29,30)(H,31,32)/b7-6-,10-9-,12-11+,16-13+/t20?,21-,22+/m0/s1

Upstream product

• 75415-34-8 (7E,9E,11Z,14Z)-(5S,6R)-5-Hydroxy-6-[2-methoxycarbonyl-2-(2,2,2-trifluoro-acetylamino)-ethylsulfanyl]-icosa-7,9,11,14-tetraenoic acid methyl ester 
• 76322-44-6 (7E,9E,11Z,14Z)-(5S,6R)-5-Hydroxy-6-[2-(methoxycarbonylmethyl-carbamoyl)-2-(2,2,2-trifluoro-acetylamino)-ethylsulfanyl]-icosa-7,9,11,14-tetraenoic acid methyl ester 
• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 
• 73427-12-0 methyl 6-formyl-5,6-trans-epoxyhexanoate 
• 102906-05-8 (Z)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hex-5-enoic acid 
• 102906-18-3 (E)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hex-5-enoic acid 
• 78377-37-4 7,8-O-isopropylidene-7(R),8-dihydroxyoct-5-enoic acid 
• 82430-34-0 7,8-O-isopropylidene-7(R),8-dihydroxyoct-5-enoic acid 
• 76322-44-6 N-trifluoroacetyl-leukotriene D₄ dimethyl ester 
• 72297-07-5 <(3Z)-nonen-1-yl>triphenylphosphonium iodide 
• 76322-44-6 Dimethyl ester of N-trifluoroacetyl leukotriene D 
• 80629-41-0 methyl ester of 5(S)-hydroperoxy-6(E)-8,11,14(Z)-eicosatetranoic acid 
• 91944-21-7 7Z,9E,11E,14Z-LTD₄ methyl ester 
• 72297-14-4 4-[(2S,3R)-((1Z,3E,5E,8Z)-3-Tetradeca-1,3,5,8-tetraenyl)-oxiranyl]-butyric acid methyl ester 

Downstream Products

• 80115-94-2 N-acetyl-leukotriene D 
• 82850-10-0 Leukotriene D4 sulfone 

Relevant academic research and scientific papers

Total synthesis of leukotrienes from butadiene

The total synthesis of leukotrienes has been achieved starting from butadiene by a palladium-catalyzed telomerization at room temperature. A Sharpless catalytic asymmetric epoxidation generated the asymmetric centers with >94% ee. Simple transformations of the key intermediate 15 produced the leukotrienes LTA4 methyl ester (4), LTC4 (1), LTD4 (2) and LTE4 (3), as well as (14S, 15S)-LTA4 methyl ester (24) and the novel [2H2]-LTA4 methyl ester (28). The use of the opposite chiral director in the Sharpless catalytic asymmetric epoxidation gave the key intermediate 15a that has been used in the synthesis of the double epimers of the leukotrienes as well as LTB4.

Method alleviating migraine headache with mast cell degranulation blocking agents

A method of preventing or alleviating a migraine headache which comprises administering a pharmaceutically effective amount of a mast cell degranulation blocking agent just prior to or during the prodromal phase of the migraine in the absence of an analgesic. The agent can also be administered in combination with a central nervous system stimulant.

CHEMICAL CONVERSION OF ARACHIDONIC ACID TO SLOW REACTING SUBSTANCES

The synthesis of slow reacting substances, leukotrienes C, D, and E, can be accomplished conveniently by a stereoselective biomimetic route.Details are provided for the conversion of 5-HPETE methyl ester 4 to leukotriene methyl ester (2) and thence to leukotrienes C and D.

SYNTHESIS OF LEUKOTRIENES - NEW SYNTHESIS OF NATURAL LEUKOTRIENE A4

The acetonides of D- or L-glyceraldehyde are chiral synthons for an efficient and versatile synthesis of the natural leukotrienes A4, C4, D4 and E4 and equally can be used to prepare the corresponding unnatural analogues.

Total synthesis of slow reacting substances (SRS). "Leukotriene C-2" (11-trans-leukotriene C) (3) and leukotriene D (4)

Syntheses are described for the "slow reacting substances" 11-trans-leukotriene C (3) (previously known as leukotriene C-2) and leukotriene D (4), the cys-gly analog of leukotriene C (2). The synthesized leukotrienes 3 and 4 were instrumental in the assignment of structure to these members of the family of naturally occuring slow reacting substances which includes also 2.

TOTAL SYNTHESIS OF SLOW REACTING SUBSTANCES (SRS's):6-EPI-LEUKOTRIENE C AND 6-EPI-LEUKOTRIENE D

6-Epi-leukotrienes C and D (3 and 4) have been synthesized unambigously via the 5(S),6(R)-epoxide (5,6-cis) wich is isomeric with leukotriene A.These 6-epi-leukotrienes are less active (especially 4) than leukotrienes C and D(1 and 2) and have not been fo