36700-45-5

Basic information

• Product Name: 8-SHOGAOL
• Synonyms: 8-SHOGAOL;1-(4-Hydroxy-3-methoxyphenyl)-4-dodecen-3-one
• CAS NO: 36700-45-5
• Molecular Formula: C19H28O3
• Molecular Weight: 304.42382
• EINECS: 200-258-5
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 36700-45-5.mol

Chemical Properties

• Boiling Point: 452.3°Cat760mmHg
• Flash Point: 154.6°C
• Appearance: /
• Density: 1.013g/cm³
• Vapor Pressure: 8.45E-09mmHg at 25°C
• Refractive Index: 1.516
• PKA: 10.01±0.20(Predicted)
• CAS DataBase Reference: 8-SHOGAOL(CAS DataBase Reference)
• NIST Chemistry Reference: 8-SHOGAOL(36700-45-5)
• EPA Substance Registry System: 8-SHOGAOL(36700-45-5)

Safety Data

• Hazardous Substances Data: 36700-45-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
8-SHOGAOL is used as an anti-inflammatory agent for its ability to inhibit COX-2, a key enzyme involved in the production of prostaglandins that contribute to inflammation and pain. This application is particularly relevant in the development of medications for conditions characterized by chronic inflammation, such as arthritis.
Used in Nutraceutical Industry:
8-SHOGAOL is used as a natural supplement for its anti-inflammatory and potential pain-relieving properties. It can be incorporated into dietary supplements and functional foods to support overall health and well-being, particularly for individuals seeking natural alternatives to manage inflammation and related discomfort.
Used in Cosmetics Industry:
8-SHOGAOL may also be used as an ingredient in the cosmetics industry, where its anti-inflammatory properties can be harnessed for products aimed at reducing skin inflammation, redness, and irritation. This application can be particularly beneficial for individuals with sensitive or acne-prone skin, as well as those seeking natural and effective skincare solutions.

InChI:InChI=1/C19H28O3/c1-3-4-5-6-7-8-9-10-17(20)13-11-16-12-14-18(21)19(15-16)22-2/h9-10,12,14-15,21H,3-8,11,13H2,1-2H3/b10-9+

Upstream product

• 77398-92-6 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dodecan-3-one 
• 336784-92-0 5-hydroxy-1-[3-methoxy-4-(tetrahydro-pyran-2-yloxy)-phenyl]-dodecan-3-one 
• 1080-12-2 Dehydrozingerone 
• 122-48-5 4-(4-hydroxy-3-methoxyphenyl)-2-butanone 
• 121-33-5 vanillin 
• 61152-59-8 4-hydroxy-4-(4-hydroxy-3-methoxyphenyl)butan-2-one 
• 124-13-0 Octanal 
• 223801-42-1 4-(3-methoxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl)butan-2-one 

Relevant articles and documents

First enantioselective synthesis of gingesulfonic acids and unequivocal determination of their absolute stereochemistry

Herein we report the first organocatalysed enantioselective synthesis of gingesulfonic acids and shogasulfonic acids via a mild and convenient aminothiourea-catalysed conjugate addition of bisulfite to the olefin moiety of α,β-unsaturated carbonyls - a technology previously reported by us. A series of optically active naturally occurring sulfonic acids are prepared in their natural and unnatural configurations, and their absolute configurations are unequivocally confirmed by single crystal X-ray diffractometry.

Kinetic Resolution of β-Hydroxy Carbonyl Compounds via Enantioselective Dehydration Using a Cation-Binding Catalyst: Facile Access to Enantiopure Chiral Aldols

A practical and highly enantioselective nonenzymatic kinetic resolution of racemic β-hydroxy carbonyl (aldol) compounds through enantioselective dehydration process was developed using a cation-binding Song's oligoethylene glycol (oligoEG) catalyst with p

Pharmaceutical compositions useful in prevention and treatment of beta-Amyloid protein-induced disease

The invention provides methods for treating beta-Amyloid protein-induced disease, pharmaceutical compositions and compounds useful for the same, and the use of these compounds for the manufacture of a medicament for treating the same. More particularly, the invention relates to the use of natural product compounds isolated from turmeric, gingko biloba, and ginger, and synthetic chemical analogues thereof, for the treatment of a beta-Amyloid protein-induced disease.

Side-chain length is important for shogaols in protecting neuronal cells from β-amyloid insult

Ten shogaols were synthesized to evaluate the importance of the side-chain length in protecting cells from βA(1-42) insult using PC12 rat pheochromocytoma and IMR-32 human neuroblastoma cells. The compounds cell protectivity against βA insult was demonstrated using 3-[4,5- dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) reduction assay. The efficacy of cell protection from βA insult by these shogaols was shown to improve as the length of the side chain increase.

A convenient one-step gingerol synthesis

Racemic 6-gingerol can be obtained in a one-pot reaction by hexanal addition to the dianion of zingerone at low temperature. Similarly, addition of octanal or decanal to the dianion provides 8-gingerol or 10-gingerol, respectively. Acid treatment of the gingerols allows for formation of the corresponding shogaols.