| Identification | Back Directory | [Name]
Sodium gualenate | [CAS]
6223-35-4 | [Synonyms]
Guai
sodium gualenate
3-Sulfonate sodium salt
Azulene sulfonate sodium
Sodium guazulene sulfonate
Guaiazulenesulfonate sodium
guaiazulene / azulene powder
SODIUM GUAIAZULENE SULFONATE
Sodium azulene sulphonate, 98%
Sodium 1,4-dimethyl-7-isopropylazulene-3-sulfonate
Sodium 7-Isopropyl-1,4-dimethylazulene-3-sulfonate
Sodium 5-isopropyl-3,8-dimethylazulene-1-sulfonate
sodium,3,8-dimethyl-5-propan-2-ylazulene-1-sulfonate
sodium 3,8-dimethyl-5-propan-2-yl-1-azulenesulfonate
1,4-DIMETHYL-7-ISOPROPYLAZULENE-3-SULFONATE SODIUM SALT
5-Isopropyl-3,8-dimethylazulene-1-sulfonic Acid Sodium Salt
7-Isopropyl-1,4-dimethyl-azulene-3-sulfonic Acid Sodium Salt | [EINECS(EC#)]
228-309-8 | [Molecular Formula]
C15H17NaO3S | [MDL Number]
MFCD00866167 | [MOL File]
6223-35-4.mol | [Molecular Weight]
300.35 |
| Questions And Answer | Back Directory | [Description]
Sodium gualenate is unstable, it will decompose under light, air oxidation and high temperature environment, and it is easy to remove the sulfonic acid group. According to existing reports, it is common for sodium azulene sulfonate to contain half or one crystal water. | [Uses]
Sodium gualenate is an active ingredient of chamomile flowers, which has strong anti-pepsin, anti-inflammatory, antibacterial, anti-allergic, and promotion of mucosal metabolism. It is mainly used to study duodenal ulcer, gastric ulcer and gastritis. | [Mechanism of action]
Sodium gualenate inhibits the release of histamine from inflammatory cells through local direct action; increases the synthesis of prostaglandin E2 in the mucosa, promotes granulation formation and epithelial cell regeneration; and can reduce the activity of pepsin. |
| Chemical Properties | Back Directory | [Melting point ]
98°C(lit.) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
DMSO : 30 mg/mL (99.88 mM) | [form ]
powder to crystaline | [color ]
Blue to Dark blue | [Merck ]
14,4554 | [InChI]
InChI=1S/C15H18O3S.Na/c1-9(2)12-6-5-10(3)15-13(8-12)11(4)7-14(15)19(16,17)18;/h5-9H,1-4H3,(H,16,17,18);/q;+1/p-1 | [InChIKey]
GEYJUFBPCGDENK-UHFFFAOYSA-M | [SMILES]
C12C(C)=CC=C(C(C)C)C=C1C(=CC=2S([O-])(=O)=O)C.[Na+] |
| Hazard Information | Back Directory | [Synthesis]
(1) Preparation of sodium 3,8-dimethyl-5-isopropylchrysanthemum-1-sulfonate
Under ice bath conditions, 4 mmol of guaiacol and 2 mL of acetic anhydride (Ac2O) were added to a 25 mL pear-shaped flask. Subsequently, a mixture of 1 mL of concentrated sulfuric acid (H2SO4) and 2 mL of acetic anhydride (Ac2O) was slowly added dropwise through a constant-pressure dropping funnel (with a drying tube fitted at the top). After the dropwise addition, the reaction mixture was stirred at room temperature for about 2 hours, during which the progress of the reaction was monitored by thin layer chromatography (TLC) until the feedstock completely disappeared. Upon completion of the reaction, the mixture solution was poured into 4 mL of water and the pH was adjusted to 8-9 by dropwise addition of sodium hydroxide (NaOH) solution.Subsequently, the mixture solution was cooled to promote the formation of a precipitate, filtration was carried out, and the precipitate was washed sequentially with cold water and petroleum ether, and was dried to give 1.05 g of a blue solid product. The yield was 87.5% and the melting point was 106-107 °C. | [in vivo]
Sodium gualenate has been frequently used for the treatment of human gastritis. Cytoprotection is defined as the main mechanism of Sodium gualenate to protect the mucosa of the stomach and the antipeptic actions in vivo have also been shown[2]. | [References]
[1] Nakamichi K, et al. Stabilization of sodium guaiazulene sulfonate in granules for tableting prepared using a twin-screw extruder. Eur J Pharm Biopharm. 2003 Nov;56(3):347-54. DOI:10.1016/s0939-6411(03)00100-0
[2] Cao T, et al. Synthesis and Biological Evaluation of 3, 8-dimethyl-5-isopropylazulene Derivatives as Anti-gastric Ulcer Agent. Chem Biol Drug Des. 2016 Aug;88(2):264-71. DOI:10.1111/cbdd.12753 |
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