[6]-Shogaol - Moligand™, 10mM in DMSO , CAS No.555-66-8

CAS: 555-66-8 Cat. No.: S424730 Molecular Weight: 276.37 Beilstein Registry Number: 2056098 EC Number: 664-006-0

GRADE & PURITY Moligand™, 10mM in DMSO

Synonyms

[6]-Shogaol;6-Shogaol | 6-Shogaol | AC-34334 | NSC752389 | NSC-752389 | Q2746448 | (E)-1-(4-Hydroxy-3- methoxyphenyl)dec-4-en-3-one | [(E)-1-(4-hydroxy-3-methoxyphenyl)-dec-4-en-3-one] | 1-(4-Hydroxy-3-methoxyphenyl)-4-dodecen-3-one, 9CI | BDBM50237536 |

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Specifications

Synonyms

[6]-Shogaol;6-Shogaol | 6-Shogaol | AC-34334 | NSC752389 | NSC-752389 | Q2746448 | (E)-1-(4-Hydroxy-3- methoxyphenyl)dec-4-en-3-one | [(E)-1-(4-hydroxy-3-methoxyphenyl)-dec-4-en-3-one] | 1-(4-Hydroxy-3-methoxyphenyl)-4-dodecen-3-one, 9CI | BDBM50237536 |

Specifications & Purity

Moligand™, 10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Names and Identifiers

• Canonical Smiles: CCCCCC=CC(=O)CCC1=CC(=C(C=C1)O)OC
• IUPAC Name: (E)-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one
• InChIKey: OQWKEEOHDMUXEO-BQYQJAHWSA-N
• 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+
• Isomeric SMILES: CCCCC/C=C/C(=O)CCC1=CC(=C(C=C1)O)OC
• WGK Germany: 3
• Alternate CAS: 23513-13-5,555-66-8
• NSC Number: 752389
• MeSH Entry Terms: (6)-shogaol;6-shogaol;shogaol
• Molecular Weight: 276.37
• Beilstein: 2056098
• Reaxy-Rn: 2056098
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2056098&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Phenols
      • Subclass Methoxyphenols

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Phenols
• Subclass: Methoxyphenols
• Intermediate Tree Nodes: Not available
• Direct Parent: Shogaols
• Alternative Parents: Phenoxy compounds Methoxybenzenes Anisoles Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids Enones Acryloyl compounds Ketones Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Shogaol - Phenoxy compound - Anisole - Phenol ether - Methoxybenzene - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Monocyclic benzene moiety - Enone - Acryloyl-group - Alpha,beta-unsaturated ketone - Ketone - Ether - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Organic oxide - Organic oxygen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as shogaols. These are ginger derivatives containing a shogaol moiety, which consists of a benzene ring bearing a dec-4-en-3-one moiety, a methoxyphenyl group, a hydroxyl group and at positions 1, 3, and 4, respectively.
• External Descriptors: Zingiber derived compounds

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

TRPV1 Tclin Transient receptor potential cation channel subfamily V member 1 (2 Activities)

Discover Target: TRPV1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

Discover Target: HTR1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX5 Tclin Arachidonate 5-lipoxygenase (6568 Activities)

Discover Target: ALOX5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

Discover Target: PTGS2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LTA4H Tchem Leukotriene A4 hydrolase (1442 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C8 Tchem Cytochrome P450 2C8 (1492 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TRPV1 Tclin Vanilloid receptor (8273 Activities)

Discover Target: TRPV1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BCHE Tclin Butyrylcholinesterase (7174 Activities)

Discover Target: BCHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

APP Tclin Amyloid-beta A4 protein (8510 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

Discover Target: CYP2D6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

Discover Target: CYP1A2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2E1 Tchem Cytochrome P450 2E1 (2174 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2A6 Tchem Cytochrome P450 2A6 (2861 Activities)

Discover Target: CYP2A6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2B6 Tchem Cytochrome P450 2B6 (1338 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HT-29 (80576 Activities)

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IMR-32 (1082 Activities)

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NCI-H1299 (3248 Activities)

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HCT-116 (91556 Activities)

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HepG2 (196354 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NLRP3 Tchem NACHT, LRR and PYD domains-containing protein 3 (908 Activities)

Discover Target: NLRP3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Abcb1b P-glycoprotein 1 (174 Activities)

Discover Target: Abcb1b

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rodentolepis nana (555 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PC-12 (7051 Activities)

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RBL-2H3 (1162 Activities)

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C6 (2371 Activities)

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BV-2 (3710 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trpa1 Transient receptor potential cation channel subfamily A member 1 (1003 Activities)

Discover Target: Trpa1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Plasma (328 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mapt Microtubule-associated protein tau (6 Activities)

Discover Target: Mapt

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Sensitive to air, light, and moisture
• Molecular Weight: 276.400 g/mol
• XLogP3: 3.700
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 276.173 Da
• Monoisotopic Mass: 276.173 Da
• Topological Polar Surface Area: 46.500 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 299.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Xiaomin Zhang, Gaofeng Hu, Chaoyang Xu, Wen Nie, Kezhou Cai, Hongmei Fang, Baocai Xu.  (2023)  Inhibition of benzo[a]pyrene formation in charcoal-grilled pork sausages by ginger and its key compounds.  JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE,  103  (6): (2838-2847).  [PMID:36700254] [10.1002/jsfa.12470]

2. Rui Bao, Qi-Long Wang, Ran Li, Michael Adu-Frimpong, Elmurat Toreniyazov, Hao Ji, Xi-Ming Xu, Jiang-Nan Yu.  (2020)  Improved oral bioavailability and target delivery of 6-shogaol via vitamin E TPGS-modified liposomes: Preparation, in-vitro and in-vivo characterizations.  JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.jddst.2020.101842]

3. Huiyun Zhang, Qilong Wang, Congyong Sun, Yuan Zhu, Qiuxuan Yang, Qiuyu Wei, Jiaxin Chen, Wenwen Deng, Michael Adu-Frimpong, Jiangnan Yu, Ximing Xu.  (2019)  Enhanced Oral Bioavailability, Anti-Tumor Activity and Hepatoprotective Effect of 6-Shogaol Loaded in a Type of Novel Micelles of Polyethylene Glycol and Linoleic Acid Conjugate.  Pharmaceutics,  11  (3): (107).  [PMID:30845761] [10.3390/pharmaceutics11030107]

4. Yanni Tai, Mintong Zhao, Feng Ding, Gelin Wu, Haibin Qu, Ping Gong, Yongjian Xie, Peng Zhou, Xingchu Gong.  (2024)  Analytical quality by design based on knowledge organization: A case study of developing an ultrahigh-performance liquid chromatography method for the detection of phenolic compounds.  PHYTOCHEMICAL ANALYSIS,      [PMID:38462508] [10.1002/pca.3343]

5. Yang Zhang, Siyi Yang, Wensi Li, Xiaoyan Li, Xiangqin Lai, Xiang Li, Wuwan Xiong, Bo Zhang.  (2025)  Optimized High-Pressure Ultrasonic-Microwave-Assisted Extraction of Gingerol from Ginger: Process Design and Performance Evaluation.  Processes,  13  (7): (2149).  [PMID:] [10.3390/pr13072149]