Sodium gualenate Chemical Properties

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+]

Safety Information

RTECS 

CO4826000

HS Code 

2908.99.1500

Sodium gualenate Usage And Synthesis

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.   

Uses

Sodium gualenate (Guaiazulenesulfonate sodium) is a hydrophilic derivative of guaiazulene with excellent anti-inflammatory and wound-healing effects mainly used for the treatment of duodenal ulcer, gastric ulcer and gastritis.

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

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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