73836-78-9

Basic information

• Product Name: LEUKOTRIENE D4
• Synonyms: glycine,n-(s-(1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-l-cyste;leukotriened;leukotriened(sub4);(5S,6R,7E,9E,11E,14E)-6-[2-amino-2-(carboxymethylcarbamoyl)ethyl]sulfanyl-5-hydroxy-icosa-7,9,11,14-tetraenoic acid;LEUKOTRIENE D4 (ETHANOL SOLUTION);N-[S-[(1R,2E,4E,6Z,9Z)-1-[(1S)-1-Hydroxy-4-carboxybutyl]-2,4,6,9-pentadecatetraene-1-yl]-L-cysteinyl]glycine;N-[S-[(1R,2E,4E,6Z,9Z)-1-[(1S)-1-Hydroxy-4-carboxybutyl]-2,4,6,9-pentadecatetren-1-yl]-L-cysteinyl]glycine;N-[S-[(1R,2E,4E,6Z,9Z)-1-[(S)-4-Carboxy-1-hydroxybutyl]-2,4,6,9-pentadecatetren-1-yl]-L-cysteinyl]glycine
• CAS NO: 73836-78-9
• Molecular Formula: C25H40N2O6S
• Molecular Weight: 496.66
• Product Categories: Arachidonic Acid Cascade;Fatty Acids;Leukotrienes;LeukotrienesLipids;Lipids in Cell Signaling
• Mol File: 73836-78-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 785.8 °C at 760 mmHg
• Flash Point: 9℃
• Appearance: /
• Density: 1.162 g/cm³
• Vapor Pressure: 1.57E-28mmHg at 25°C
• Refractive Index: 1.558
• Storage Temp.: −70°C
• PKA: 3.03±0.10(Predicted)
• CAS DataBase Reference: LEUKOTRIENE D4(CAS DataBase Reference)
• NIST Chemistry Reference: LEUKOTRIENE D4(73836-78-9)
• EPA Substance Registry System: LEUKOTRIENE D4(73836-78-9)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45
• RIDADR: UN 1230 3/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 73836-78-9(Hazardous Substances Data)

Usage

Description

Leukotriene D4 (LTD4) is an active metabolite of LTC4 (Item Nos. 20210 | 10007241) and a constituent of slow-reacting substance of anaphylaxis (SRS-A). It is formed via metabolism of LTC4 by γ-glutamyl transpeptidase. Like LTC4, LTD4 (0.01-0.1 pM) induces contractions in isolated guinea pig parenchymal strips and tracheal spirals. In vivo, LTD4 increases insufflation pressure, a marker of bronchoconstriction, in anesthetized guinea pigs by 100% when administered at a dose of 89 pmol per animal. It also increases vascular permeability in guinea pig skin when administered intradermally at a dose of 0.1 pmol per animal.

Uses

LTD4 (Leukotriene D4) is a member of the leukotriene family shown to be a potent contractor of smooth muscle.

Definition

ChEBI: A leukotriene that is (7E,9E,11Z,14Z)-icosa-7,9,11,14-tetraenoic acid substituted by a hydroxy group at position 5 (5S) and a L-cysteinylglycinyl group at position 6 (6R).

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

• 75290-62-9 N-(N-trifluoroacetylcysteinyl)-glycine methyl ester 
• 76738-49-3 5S,6R-6-epi-Leukotriene A₄ methyl ester 
• 76738-47-1 methyl 5-(S),6-(S)-oxido-7-oxoheptanoate 
• 76738-48-2 methyl 10-formyl-5(S),6(S)-oxido-7(E),9(E)-decadienoate 
• 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 
• 73958-01-7 9-oxo-5,6-trans-epoxynon-7(E)-enoate 
• 78377-38-5 (E)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hex-5-enoic acid methyl ester 

Downstream Products

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

Relevant articles and documents

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.

Syntheses of 7Z, 9E, 14Z-leukotrienes

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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.