Shogaol

[6]-Shogaol

Names
Preferred IUPAC name (4E)-1-(4-Hydroxy-3-methoxyphenyl)dec-4-en-3-one
Other names [6]-Shogaol (E)-[6]-Shogaol Enexasogaol
Identifiers
CAS Number	23513-13-5  Y 555-66-8 (non-specific) Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL25948  N
ChemSpider	4445106  N
PubChem CID	5281794
UNII	83DNB5FIRF  N
InChI InChI=1S/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3/b8-7+ N Key: OQWKEEOHDMUXEO-BQYQJAHWSA-N N InChI=1/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3/b8-7+ Key: OQWKEEOHDMUXEO-BQYQJAHWBO
SMILES CCCCCC=CC(=O)CCC1=CC(=C(C=C1)O)OC
Properties
Chemical formula	C17H24O3
Molar mass	276.376 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

Shogaol
Heat	Very hot (chemical)
Scoville scale	160,000 [1] SHU

Shogaols are pungent constituents of ginger similar in chemical structure to gingerol. The most common of the group is [6]-shogaol. Like zingerone, it is produced when ginger is dried or cooked. ^[2] Moreover, shogaol (and gingerol) are converted to other constituents when heat is applied over time, which is why ginger loses its spiciness as it is cooked.

The name shogaol is derived from the Japanese name for ginger (生姜、shōga).

Shogaol is rated 160,000 SHU on the Scoville scale. ^[1] When compared to other pungent compounds, shogaol is moderately more pungent than piperine, but 100 times less than capsaicin.

Compound	Scoville Heat Units (SHU)
Capsaicin	16,000,000 [3]
[6]-Shogaol	160,000
Piperine	100,000
[6]-Gingerol	60,000

Shogaols group

[4]-Shogaol, [8]-shogaol, [10]-shogaol, and [12]-shogaol (all found in ginger) together constitute the group shogaols. There also exist in ginger cultivars methylated shogaols: methyl [6]-shogaol and methyl [8]-shogaol, respectively. ^[4]

Shogaols are artifacts formed during storage or through excess heat, probably created by a dehydration reaction of the gingerols. The ratio of shogaols to gingerols sometimes is taken as an indication of product quality. ^[5]

[8]-shogaol

[10]-shogaol

Synthesis

A possible synthesis starts with a Claisen condensation of vanillin and acetone, producing dehydrozingerone. Afterwards the product reacts in an aldol condensation with hexanal in tetrahydrofurane to 6-dehydroshogaol and 6-dehydrogingerol. Latter can be hydrogenated to [6]-gingerol by a catalyst. In the last step hydrochloric acid is added to get the desired [6]-shogaol. ^[6]

Possible synthesis of [6]-shogaol starting from vanillin

References

1. Compton, Richard G.; Batchelor-McAuley, Christopher; Ngamchuea, Kamonwad; Chaisiwamongkhol, Korbua (2016-10-31). "Electrochemical detection and quantification of gingerol species in ginger (Zingiber officinale) using multiwalled carbon nanotube modified electrodes". Analyst. 141 (22): 6321–6328. Bibcode:2016Ana...141.6321C. doi:10.1039/C6AN02254E. ISSN   1364-5528. PMID   27774555. S2CID   40241982.
2. Harold McGee (2004). On Food and Cooking: The Science and Lore of the Kitchen (2nd ed.). New York: Scribner. pp. 425–426.
3. Govindarajan, Sathyanarayana (1991). "Capsicum — Production, Technology, Chemistry, and Quality. Part V. Impact on Physiology, Pharmacology, Nutrition, and Metabolism; Structure, Pungency, Pain, and Desensitization Sequences". Critical Reviews in Food Science and Nutrition. 29 (6): 435–474. doi:10.1080/10408399109527536. PMID   2039598.
4. Tanaka, K.; Arita, M.; Sakurai, H.; Ono, N.; Tezuka, Y. (2015). "Analysis of Chemical Properties of Edible and Medicinal Ginger by Metabolomics Approach : Table 1". BioMed Research International. doi: 10.1155/2015/671058 . PMC   4606115 . PMID   26495311 . Retrieved 3 December 2016.
5. NSF International Determination of Gingerols and Shogaols in Zingiber officinale rhizome and powdered extract by High-Performance Liquid Chromatography^{[ full citation needed ]}
6. Hung-Cheng Shih; et al. (March 2014). "Synthesis of Analogues of Gingerol and Shogaol, the Active Pungent Principles from the Rhizomes of Zingiber officinale and Evaluation of Their Anti-Platelet Aggregation Effects". International Journal of Molecular Sciences . 15 (3): 3926–3951. doi: 10.3390/ijms15033926 . PMC   3975376 . PMID   24599082.