Shogaol (6-Shogaol)
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MedKoo CAT#: 326663

CAS#: 555-66-8

Description: Shogaol, also known as (6)-shogaol, is a pungent constituent of ginger similar in chemical structure to gingerol. Like zingerone, it is produced when ginger is dried or cooked. 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. Among ginger constituents, it has a very strong antitussive (anti-cough) effect. Both shogaol and gingerols reduced blood pressure and gastric contraction. Shogaol has been shown to induce apoptosis (kill) in human colorectal carcinoma cells via reactive oxygen species. It is broken down into 16 metabolites via the mercapturic acid pathway. Acetylcysteine was found to reduce effectiveness of shogaol's apoptotic properties.

Chemical Structure

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Shogaol (6-Shogaol)
CAS# 555-66-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 326663
Name: Shogaol (6-Shogaol)
CAS#: 555-66-8
Chemical Formula: C17H24O3
Exact Mass: 276.17
Molecular Weight: 276.380
Elemental Analysis: C, 73.88; H, 8.75; O, 17.37

Price and Availability

Size Price Availability Quantity
200mg USD 950
500mg USD 1650
1g USD 2650
2g USD 3850
5g USD 6950
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Synonym: Shogaol; 6-Shogaol.

IUPAC/Chemical Name: 1-(4-Hydroxy-3-methoxyphenyl)-4-decen-3-one

InChi Key: OQWKEEOHDMUXEO-BQYQJAHWSA-N

InChi Code: 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+

SMILES Code: CCCCC/C=C/C(CCC1=CC=C(O)C(OC)=C1)=O

Appearance: Yellow, viscous oil in pure form (supplied as 200mg / mL ethanol solution)

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, DMF, and ethanol

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: 6-shogaol exhibits a variety of biological activities including anticancer, anti-inflammation, and anti-oxidation.
In vitro activity: 6-shogaol promoted oxidative-stress-mediated apoptosis in HeLa cells. 6-shogaol specifically inhibited purified TrxR1 activity by targeting selenocysteine residues was more cytotoxic to HeLa cells than normal cells. The molecular mechanism of 6-shogaol-mediated apoptosis involves TrxR inhibition, followed by an outburst of ROS production. Reference: Int J Mol Sci. 2023 Mar 4;24(5):4966. https://pubmed.ncbi.nlm.nih.gov/36902397/
In vivo activity: 6-shogaol could be a potential phytochemical and act as a chemopreventive agent in benzopyrene (BaP)-induced lung cancer by enhancing PRDX1 expression. In a mouse model of BaP exposure, 6-shogaol prevented weight loss, increased lung weight, and the total number of tumors. 6-shogaol treatment reverted the activity of BaP-induced lipid peroxidation and antioxidants and impeded the phosphorylation of MAPK family proteins. Reference: Environ Toxicol. 2023 Aug 28. https://pubmed.ncbi.nlm.nih.gov/37638803/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 20.0 72.36
DMSO 20.0 72.36
Ethanol 20.0 72.36

Preparing Stock Solutions

The following data is based on the product molecular weight 276.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Peng S, Yu S, Zhang J, Zhang J. 6-Shogaol as a Novel Thioredoxin Reductase Inhibitor Induces Oxidative-Stress-Mediated Apoptosis in HeLa Cells. Int J Mol Sci. 2023 Mar 4;24(5):4966. doi: 10.3390/ijms24054966. PMID: 36902397; PMCID: PMC10003455. 2. Ozkan T, Hekmatshoar Y, Pamuk H, Ozcan M, Yaman G, Yagiz GC, Akdemir C, Sunguroglu A. Cytotoxic effect of 6-Shogaol in Imatinib sensitive and resistant K562 cells. Mol Biol Rep. 2021 Feb;48(2):1625-1631. doi: 10.1007/s11033-021-06141-2. Epub 2021 Jan 30. PMID: 33515349. 3. Pan S, Li Y, Zhang J. 6-Shogaol prevents benzo (A) pyrene-exposed lung carcinogenesis via modulating PRDX1-associated oxidative stress, inflammation, and proliferation in mouse models. Environ Toxicol. 2023 Aug 28. doi: 10.1002/tox.23946. Epub ahead of print. PMID: 37638803. 4. Huh E, Choi JG, Choi Y, Ju IG, Noh D, Shin DY, Kim DH, Park HJ, Oh MS. 6-Shogaol, an Active Ingredient of Ginger, Improves Intestinal and Brain Abnormalities in Proteus Mirabilis-Induced Parkinson's Disease Mouse Model. Biomol Ther (Seoul). 2023 Jul 1;31(4):417-424. doi: 10.4062/biomolther.2023.098. Epub 2023 Jun 20. PMID: 37337830; PMCID: PMC10315336.
In vitro protocol: 1. Peng S, Yu S, Zhang J, Zhang J. 6-Shogaol as a Novel Thioredoxin Reductase Inhibitor Induces Oxidative-Stress-Mediated Apoptosis in HeLa Cells. Int J Mol Sci. 2023 Mar 4;24(5):4966. doi: 10.3390/ijms24054966. PMID: 36902397; PMCID: PMC10003455. 2. Ozkan T, Hekmatshoar Y, Pamuk H, Ozcan M, Yaman G, Yagiz GC, Akdemir C, Sunguroglu A. Cytotoxic effect of 6-Shogaol in Imatinib sensitive and resistant K562 cells. Mol Biol Rep. 2021 Feb;48(2):1625-1631. doi: 10.1007/s11033-021-06141-2. Epub 2021 Jan 30. PMID: 33515349.
In vivo protocol: 1. Pan S, Li Y, Zhang J. 6-Shogaol prevents benzo (A) pyrene-exposed lung carcinogenesis via modulating PRDX1-associated oxidative stress, inflammation, and proliferation in mouse models. Environ Toxicol. 2023 Aug 28. doi: 10.1002/tox.23946. Epub ahead of print. PMID: 37638803. 2. Huh E, Choi JG, Choi Y, Ju IG, Noh D, Shin DY, Kim DH, Park HJ, Oh MS. 6-Shogaol, an Active Ingredient of Ginger, Improves Intestinal and Brain Abnormalities in Proteus Mirabilis-Induced Parkinson's Disease Mouse Model. Biomol Ther (Seoul). 2023 Jul 1;31(4):417-424. doi: 10.4062/biomolther.2023.098. Epub 2023 Jun 20. PMID: 37337830; PMCID: PMC10315336.

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1: Zhu Y, Wang P, Zhao Y, Yang C, Clark A, Leung T, Chen X, Sang S. Synthesis, evaluation, and metabolism of novel [6]-shogaol derivatives as potent Nrf2 activators. Free Radic Biol Med. 2016 Jun;95:243-54. doi: 10.1016/j.freeradbiomed.2016.03.026. Epub 2016 Mar 25. PubMed PMID: 27021962.

2: Kathiresan S, Govindhan A. [6]-Shogaol, a Novel Chemopreventor in 7,12-Dimethylbenz[a]anthracene-induced Hamster Buccal Pouch Carcinogenesis. Phytother Res. 2016 Apr;30(4):646-53. doi: 10.1002/ptr.5574. Epub 2016 Feb 3. PubMed PMID: 26840796.

3: Ray A, Vasudevan S, Sengupta S. 6-Shogaol Inhibits Breast Cancer Cells and Stem Cell-Like Spheroids by Modulation of Notch Signaling Pathway and Induction of Autophagic Cell Death. PLoS One. 2015 Sep 10;10(9):e0137614. doi: 10.1371/journal.pone.0137614. eCollection 2015. PubMed PMID: 26355461; PubMed Central PMCID: PMC4565635.

4: Ghasemzadeh A, Jaafar HZ, Rahmat A. Optimization protocol for the extraction of 6-gingerol and 6-shogaol from Zingiber officinale var. rubrum Theilade and improving antioxidant and anticancer activity using response surface methodology. BMC Complement Altern Med. 2015 Jul 30;15:258. doi: 10.1186/s12906-015-0718-0. PubMed PMID: 26223685; PubMed Central PMCID: PMC4520084.

5: Peng S, Yao J, Liu Y, Duan D, Zhang X, Fang J. Activation of Nrf2 target enzymes conferring protection against oxidative stress in PC12 cells by ginger principal constituent 6-shogaol. Food Funct. 2015 Aug;6(8):2813-23. doi: 10.1039/c5fo00214a. Epub 2015 Jul 14. PubMed PMID: 26169810.

6: Qi LW, Zhang Z, Zhang CF, Anderson S, Liu Q, Yuan CS, Wang CZ. Anti-Colon Cancer Effects of 6-Shogaol Through G2/M Cell Cycle Arrest by p53/p21-cdc2/cdc25A Crosstalk. Am J Chin Med. 2015;43(4):743-56. doi: 10.1142/S0192415X15500469. Epub 2015 Jun 28. PubMed PMID: 26119958.

7: Wu JJ, Omar HA, Lee YR, Teng YN, Chen PS, Chen YC, Huang HS, Lee KH, Hung JH. 6-Shogaol induces cell cycle arrest and apoptosis in human hepatoma cells through pleiotropic mechanisms. Eur J Pharmacol. 2015 Sep 5;762:449-58. doi: 10.1016/j.ejphar.2015.06.032. Epub 2015 Jun 20. PubMed PMID: 26101062.

8: Feroz SR, Mohamad SB, Lee GS, Malek SN, Tayyab S. Supramolecular interaction of 6-shogaol, a therapeutic agent of Zingiber officinale with human serum albumin as elucidated by spectroscopic, calorimetric and molecular docking methods. Phytomedicine. 2015 Jun 1;22(6):621-30. doi: 10.1016/j.phymed.2015.03.016. Epub 2015 Apr 9. PubMed PMID: 26055127.

9: Wu CH, Hong BH, Ho CT, Yen GC. Targeting cancer stem cells in breast cancer: potential anticancer properties of 6-shogaol and pterostilbene. J Agric Food Chem. 2015 Mar 11;63(9):2432-41. doi: 10.1021/acs.jafc.5b00002. Epub 2015 Feb 25. PubMed PMID: 25686711.

10: Singh VK, Doharey PK, Kumar V, Saxena JK, Siddiqi MI, Rathaur S, Narender T. Synthesis, molecular docking and Brugia malayi thymidylate kinase (BmTMK) enzyme inhibition study of novel derivatives of [6]-shogaol. Eur J Med Chem. 2015 Mar 26;93:74-82. doi: 10.1016/j.ejmech.2015.01.035. Epub 2015 Jan 20. PubMed PMID: 25659753.

11: Liu R, Heiss EH, Sider N, Schinkovitz A, Gröblacher B, Guo D, Bucar F, Bauer R, Dirsch VM, Atanasov AG. Identification and characterization of [6]-shogaol from ginger as inhibitor of vascular smooth muscle cell proliferation. Mol Nutr Food Res. 2015 May;59(5):843-52. doi: 10.1002/mnfr.201400791. Epub 2015 Mar 16. PubMed PMID: 25631547; PubMed Central PMCID: PMC4573514.

12: Hsu YL, Hung JY, Tsai YM, Tsai EM, Huang MS, Hou MF, Kuo PL. 6-shogaol, an active constituent of dietary ginger, impairs cancer development and lung metastasis by inhibiting the secretion of CC-chemokine ligand 2 (CCL2) in tumor-associated dendritic cells. J Agric Food Chem. 2015 Feb 18;63(6):1730-8. doi: 10.1021/jf504934m. Epub 2015 Feb 9. PubMed PMID: 25621970.

13: Han MA, Woo SM, Min KJ, Kim S, Park JW, Kim DE, Kim SH, Choi YH, Kwon TK. 6-Shogaol enhances renal carcinoma Caki cells to TRAIL-induced apoptosis through reactive oxygen species-mediated cytochrome c release and down-regulation of c-FLIP(L) expression. Chem Biol Interact. 2015 Feb 25;228:69-78. doi: 10.1016/j.cbi.2015.01.020. Epub 2015 Jan 22. PubMed PMID: 25619640.

14: Chen H, Fu J, Chen H, Hu Y, Soroka DN, Prigge JR, Schmidt EE, Yan F, Major MB, Chen X, Sang S. Ginger compound [6]-shogaol and its cysteine-conjugated metabolite (M2) activate Nrf2 in colon epithelial cells in vitro and in vivo. Chem Res Toxicol. 2014 Sep 15;27(9):1575-85. doi: 10.1021/tx500211x. Epub 2014 Sep 2. PubMed PMID: 25148906; PubMed Central PMCID: PMC4176387.

15: Huang HC, Chang SJ, Wu CY, Ke HJ, Chang TM. [6]-Shogaol inhibits α-MSH-induced melanogenesis through the acceleration of ERK and PI3K/Akt-mediated MITF degradation. Biomed Res Int. 2014;2014:842569. doi: 10.1155/2014/842569. Epub 2014 Jun 19. PubMed PMID: 25045707; PubMed Central PMCID: PMC4090493.

16: Kim SM, Kim C, Bae H, Lee JH, Baek SH, Nam D, Chung WS, Shim BS, Lee SG, Kim SH, Sethi G, Ahn KS. 6-Shogaol exerts anti-proliferative and pro-apoptotic effects through the modulation of STAT3 and MAPKs signaling pathways. Mol Carcinog. 2015 Oct;54(10):1132-46. doi: 10.1002/mc.22184. Epub 2014 Jun 24. PubMed PMID: 24962868.

17: Yoshida K, Satsu H, Mikubo A, Ogiwara H, Yakabe T, Inakuma T, Shimizu M. 6-shogaol, a major compound in ginger, induces aryl hydrocarbon receptor-mediated transcriptional activity and gene expression. J Agric Food Chem. 2014 Jun 18;62(24):5492-9. doi: 10.1021/jf405146j. Epub 2014 Jun 5. PubMed PMID: 24857157.

18: Moon M, Kim HG, Choi JG, Oh H, Lee PK, Ha SK, Kim SY, Park Y, Huh Y, Oh MS. 6-Shogaol, an active constituent of ginger, attenuates neuroinflammation and cognitive deficits in animal models of dementia. Biochem Biophys Res Commun. 2014 Jun 20;449(1):8-13. doi: 10.1016/j.bbrc.2014.04.121. Epub 2014 May 2. PubMed PMID: 24796668.

19: Saha A, Blando J, Silver E, Beltran L, Sessler J, DiGiovanni J. 6-Shogaol from dried ginger inhibits growth of prostate cancer cells both in vitro and in vivo through inhibition of STAT3 and NF-κB signaling. Cancer Prev Res (Phila). 2014 Jun;7(6):627-38. doi: 10.1158/1940-6207.CAPR-13-0420. Epub 2014 Apr 1. PubMed PMID: 24691500.

20: Kim SC, Lee JR, Park SJ. Role of 6-shogaol in tert -butyl hydroperoxide-induced apoptosis of HepG2 cells. Pharmacology. 2014;93(3-4):137-44. doi: 10.1159/000360090. Epub 2014 Mar 18. PubMed PMID: 24662601.