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2-Methyl-2-butendis?ure, (Z)-

Citraconic acid Struktur
498-23-7
CAS-Nr.
498-23-7
Bezeichnung:
2-Methyl-2-butendis?ure, (Z)-
Englisch Name:
Citraconic acid
Synonyma:
Citraconic;METHYLMALEIC ACID;2-Methylmaleic acid;2-METHYL-2-BUTENEDIOIC ACID;(Z)-2-Methyl-2-butenedioic acid;CITRACONIC ACID;Citracoinc acid;methyl-maleicaci;Citraconicacid,98+%;kyselinacitrakonova
CBNumber:
CB3343788
Summenformel:
C5H6O4
Molgewicht:
130.1
MOL-Datei:
498-23-7.mol

2-Methyl-2-butendis?ure, (Z)- Eigenschaften

Schmelzpunkt:
88-94 °C (lit.)
Siedepunkt:
160.75°C (rough estimate)
Dichte
1,62 g/cm3
Brechungsindex
1.4502 (estimate)
storage temp. 
Hygroscopic, -20°C Freezer, Under inert atmosphere
L?slichkeit
DMSO (Sparingly, Sonicated), Water (Slightly)
pka
pK1:2.29(0);pK2:6.15(+1) (25°C)
Aggregatzustand
Crystalline Powder
Farbe
White to light beige
Wasserl?slichkeit
FREELY SOLUBLE
Sensitive 
Hygroscopic
Merck 
14,2321
BRN 
1722679
Henry's Law Constant
3.6×107 mol/(m3Pa) at 25℃, Yaws (2003)
Stabilit?t:
Hygroscopic
InChI
1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2-
InChIKey
HNEGQIOMVPPMNR-IHWYPQMZSA-N
SMILES
C\C(=C\C(O)=O)C(O)=O
CAS Datenbank
498-23-7(CAS DataBase Reference)
NIST chemische Informationen
2-Butenedioic acid, 2-methyl-, (Z)-(498-23-7)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher Xn
R-S?tze: 22-36/37/38
S-S?tze: 36-37/39-26
RIDADR  2811
WGK Germany  3
RTECS-Nr. GE6650000
HazardClass  6.1(b)
PackingGroup  III
HS Code  29171900
Speicherklasse 11 - Combustible Solids
Hazard Classifications Acute Tox. 4 Oral
Toxizit?t LD50 in rats, mice (mg/kg): 1320, 2260 orally (Jenner)
Bildanzeige (GHS) Exclamation Mark (GHS07)Skull and Crossbones (GHS06)
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H301 Giftig bei Verschlucken. Akute Toxizit?t oral Kategorie 3 Achtung P264, P270, P301+P310, P321, P330,P405, P501
H302 Gesundheitssch?dlich bei Verschlucken. Akute Toxizit?t oral Kategorie 4 Warnung P264, P270, P301+P312, P330, P501
Sicherheit
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P270 Bei Gebrauch nicht essen, trinken oder rauchen.
P321 Besondere Behandlung
P405 Unter Verschluss aufbewahren.
P501 Inhalt/Beh?lter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

2-Methyl-2-butendis?ure, (Z)- Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R22:Gesundheitssch?dlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

S-S?tze Betriebsanweisung:

S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.

Chemische Eigenschaften

white to light beige crystalline powder

Verwenden

Citraconic acid is used in synthetic or copolymer oils, in treating metals for adhesion of polyolefins, and in thermoplastics.

Biologische Aktivit?t

Citraconic acid is a compound with multiple biological activities that can mitigate oxidative damage and activate the Nrf2 pathway [1]. Furthermore, it exerts a protective effect against radiation-induced intestinal injury (RIII). Studies have shown that treatment with citraconic acid suppresses the radiation-induced elevation of IL-6 and TNF-α levels. It increased the number of Ki67-positive and Lgr5-positive cells, increased the number of goblet cells and mucus secretion, and restored the expression of tight junction proteins ZO-1 and occludin, thereby improving histological damage [2]. It also plays a role in alleviating endometrial fibrosis, offering a new approach for the treatment of endometriosis [3].

Synthese

Citraconic acid can be obtained by reacting citraconic anhydride with distilled water, yielding a 94% yield. The specific reaction steps are as follows:
(1) Take a clean 100-millilitre beaker and add 22.4 g (0.2 mol) of citraconic anhydride. Then, add 4 ml (0.22 moles) of distilled water dropwise to the beaker.
(2) Place the mixture on a hotplate and stir until a homogeneous solution is formed.
(3) Cover the beaker with a bell-shaped glass lid, then leave it to stand at room temperature for 48 hours. The mixture will solidify completely. This yields 26 g of crude solid.
(4) Purification: Grind the solid obtained in (3) to a very fine powder in a mortar, wash with 50 ml of cold benzene, allow to air-dry, and then vacuum-dry for 24 hours in a vacuum desiccator containing phosphorus pentoxide. This yields 24.4 g of citraconic acid, with a melting point of 92–93 °C.
synthesis of Citraconic acid

l?uterung methode

Steam distil and crystallise it from EtOH/ligroin. [Beilstein 2 H 768, 2 I 309, 2 II 652, 2 III 1938, 2 IV 2230.]

2-Methyl-2-butendis?ure, (Z)- Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


2-Methyl-2-butendis?ure, (Z)- Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 184)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
GuiZhou DoSincerely biological technology Co.,Ltd.
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+8618531123677
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Hebei Chuanghai Biotechnology Co., Ltd
+8615531151365
mina@chuanghaibio.com China 18126 58
Henan Fengda Chemical Co., Ltd
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info@fdachem.com China 20122 58
Alchem Pharmtech,Inc.
8485655694
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marketing@targetmol.com United States 32466 58
Hefei TNJ Chemical Industry Co.,Ltd.
+86-0551-65418671 +8618949823763
sales@tnjchem.com China 34563 58
Dayang Chem (Hangzhou) Co.,Ltd.
+86-0571-88938639 +8617705817739
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Hangzhou MolCore BioPharmatech Co.,Ltd.
+86-057181025280; +8617767106207
sales@molcore.com China 49734 58

498-23-7(2-Methyl-2-butendis?ure, (Z)-)Verwandte Suche:


  • (2Z)-2-Methyl-2-butenedioic acid
  • Kyselina citrakonova
  • kyselinacitrakonova
  • Maleic acid, methyl-
  • CITRACONIC ACID
  • cis-methylbutenedioic acid
  • methyl-maleicaci
  • Citraconicacid,98+%
  • Citraconic acid, 99+%
  • (Z)-2-Methylbut-2-enedioic acid
  • 2-Butenedioic acid, 2-methyl-
  • cis-Citraconic acid
  • Citraconic acid, 99+% 25GR
  • Citraconic acid 98%
  • (Z)-2-methylbut-2-enedioate
  • Citraconic Acid >
  • 2-Butenedioic acid,2-methyl-, (2Z)-
  • (E)-2-methyl-2-butenedioate
  • 2-Methylmaleic acid
  • METHYLMALEIC ACID
  • Citracoinc acid
  • Citraconic acid, 10 mM in DMSO
  • (Z)-2-Methyl-2-butenedioic acid
  • 2-METHYL-2-BUTENEDIOIC ACID
  • Citraconic
  • 498-23-7
  • HOOCCHCCH3COOH
  • 498237
  • CH3CCO2HCHCO2H
  • Carboxylic Acids
  • Carbonyl Compounds
  • C1 to C5
  • Building Blocks
  • Organic Building Blocks
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