Geniposide - analytical standard, Moligand™, ≥98% , CAS No.24512-63-8

CAS: 24512-63-8 Cat. No.: G101668 Molecular Weight: 388.37 EC Number: 683-175-1

GRADE & PURITY Analytical standard, Moligand™, ≥98%

Synonyms

DTXSID101318419 | Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, (1S,4aS,7aS)- | (1S)-1alpha-(beta-D-Glucopyranosyloxy)-7-(hydroxymethyl)-1,4aalpha,5,7aalpha-tetrahydrocyclopenta[c

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

DTXSID101318419 | Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1, 4a, 5, 7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, (1S, 4aS, 7aS)- | (1S)-1alpha-(beta-D-Glucopyranosyloxy)-7-(hydroxymethyl)-1, 4aalpha, 5, 7aalpha-tetrahydrocyclopenta[c

Specifications & Purity

analytical standard, Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Geniposide is an iridoid glycoside with a variety of biological activities including neuroprotective, anti-diabetic, antiproliferative, and antioxidative activity. Geniposide has been shown to regulate Nrf2 translocation and upregulate downstream antioxid

Storage

Protected from light, Store at -20°C

Shipped In

Ice chest + Ice pads

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

Grade

Analytical standard, Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 528769867
• Canonical Smiles: COC(=O)C1=COC(C2C1CC=C2CO)OC3C(C(C(C(O3)CO)O)O)O
• IUPAC Name: methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• InChIKey: IBFYXTRXDNAPMM-BVTMAQQCSA-N
• INCHI: 1S/C17H24O10/c1-24-15(23)9-6-25-16(11-7(4-18)2-3-8(9)11)27-17-14(22)13(21)12(20)10(5-19)26-17/h2,6,8,10-14,16-22H,3-5H2,1H3/t8-,10-,11-,12-,13+,14-,16+,17+/m1/s1
• Isomeric SMILES: COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC=C2CO)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• WGK Germany: 3
• Molecular Weight: 388.37
• Reaxy-Rn: 33425786
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=33425786&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Terpene glycosides

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Terpene glycosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Iridoid O-glycosides
• Alternative Parents: Hexoses O-glycosyl compounds Bicyclic monoterpenoids Iridoids and derivatives Oxanes Methyl esters Enoate esters Vinylogous esters Secondary alcohols Oxacyclic compounds Polyols Monocarboxylic acids and derivatives Acetals Organic oxides Primary alcohols Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Iridoid o-glycoside - Hexose monosaccharide - Glycosyl compound - Iridoid-skeleton - O-glycosyl compound - Bicyclic monoterpenoid - Monoterpenoid - Monosaccharide - Oxane - Vinylogous ester - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Methyl ester - Carboxylic acid ester - Secondary alcohol - Acetal - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Oxacycle - Carboxylic acid derivative - Polyol - Organooxygen compound - Alcohol - Hydrocarbon derivative - Organic oxide - Carbonyl group - Primary alcohol - Organic oxygen compound - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.
• External Descriptors: Iridoids

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)

XDH Tclin Xanthine dehydrogenase (1038 Activities)

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PTPN2 Tchem T-cell protein-tyrosine phosphatase (1317 Activities)

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PTPN11 Tchem Protein-tyrosine phosphatase 2C (2297 Activities)

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Raji (5516 Activities)

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dsDNA (365 Activities)

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quadruplex DNA (2700 Activities)

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HK-2 (249 Activities)

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

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Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)

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pol Human immunodeficiency virus type 1 integrase (9041 Activities)

Discover Target: pol

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Mus musculus (284745 Activities)

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Hepatitis C virus (23859 Activities)

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Enterovirus A71 (1246 Activities)

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RAW264.7 (28094 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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Drosophila (190 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Light sensitive
• Specific Rotation[α]: 15° (C=1,EtOH)
• Melt Point(°C): 162°C
• Molecular Weight: 388.400 g/mol
• XLogP3: -2.300
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 388.137 Da
• Monoisotopic Mass: 388.137 Da
• Topological Polar Surface Area: 155.000 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 617.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yuxin Gan, Chenyu Wang, Chenfeng Xu, Pingping Zhang, Shutong Chen, Lei Tang, Junbing Zhang, Huahao Zhang, Shenhua Jiang.  (2023)  Simultaneous extraction of crocin and geniposide from gardenia fruits (Gardenia jasminoides Ellis) by probe-type ultrasound-assisted natural deep eutectic solvents and their inhibition effects on low density lipoprotein oxidation.  ULTRASONICS SONOCHEMISTRY,      [PMID:37913593] [10.1016/j.ultsonch.2023.106658]

2. Xiaoju Zhuge, Xiaosheng Jin, Tingting Ji, Rongzhou Li, Liwei Xue, Weilai Yu, Zijiao Quan, Haibin Tong, Fang Xu.  (2023)  Geniposide ameliorates dextran sulfate sodium-induced ulcerative colitis via KEAP1-Nrf2 signaling pathway.  JOURNAL OF ETHNOPHARMACOLOGY,      [PMID:37187359] [10.1016/j.jep.2023.116626]

3. Ling Li, Ling Zhou, Gongshuai Song, Danli Wang, Gongnian Xiao, Fuping Zheng, Jinyan Gong.  (2023)  High efficiency biosynthesis of gardenia blue and red pigment by lactic acid bacteria: A great potential for natural color pigments.  FOOD CHEMISTRY,      [PMID:36924722] [10.1016/j.foodchem.2023.135868]

4. Jiaxin Li, Hengju Ge, Yang Xu, Jiahong Xie, Fujie Yan, Wei Chen.  (2022)  Geniposide Alleviates Oxidative Damage in Hepatocytes through Regulating miR-27b-3p/Nrf2 Axis.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:36084288] [10.1021/acs.jafc.2c03856]

5. Sitong Lu, Zhaoyu Zhang, Youling Liang, Qingkun Zhong, Guangfa Li, Zhang Hu.  (2022)  Iridoid Glycosides from Phlomis Medicinalis Diels: Optimized Extraction and Hemostasis Evaluation.  CHEMISTRY & BIODIVERSITY,  19  (5): (e202100936).  [PMID:35502889] [10.1002/cbdv.202100936]

6. Tang Liqin, Liu Haocheng, Wen Jing, Xu Yujuan, Tian Wenni, Li Lu, Yu Yuanshan, Lin Xian, Fu Manqin.  (2021)  Study on ultrahigh-pressure extraction technology on properties of yellow extract from gardenia fruit.  JOURNAL OF FOOD COMPOSITION AND ANALYSIS,      [PMID:] [10.1016/j.jfca.2021.104186]

7. Zilong Chen, Hongdong Liu, Jie Chen, Weifeng Zhu, Yong Liu, Jianxin Min, Xiaotian Chen, Bin Li, Xin Yang.  (2021)  Separation and enrichment of sibiskoside from Sibiraea angustat with magnetic surface dummy template molecularly imprinted polymers.  JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES,      [PMID:34224966] [10.1016/j.jchromb.2021.122767]

8. Dong-Xing Liu, Di Zhang, Wei-Min Hu, Yan-Fang Chang, Xiao-Hui Wang, Lin Li.  (2021)  Geniposide protection against Aβ1-42 toxicity correlates with mTOR inhibition and enhancement of autophagy.  Journal of Integrative Neuroscience,  20  (1): (67-75).  [PMID:33834692] [10.31083/j.jin.2021.01.242]

9. Ma Chongyang, Wang Xueqian, Xu Tian, Zhang Shuang, Liu Shuling, Zhai Changming, Wang Zisong, Mu Jie, Li Changxiang, Cheng Fafeng, Wang Qingguo.  (2020)  An Integrative Pharmacology-Based Analysis of Refined Qingkailing Injection Against Cerebral Ischemic Stroke: A Novel Combination of Baicalin, Geniposide, Cholic Acid, and Hyodeoxycholic Acid.  Frontiers in Pharmacology,      [PMID:32457601] [10.3389/fphar.2020.00519]

10. Sen Yang, Ge Kuang, Rong Jiang, Shengwang Wu, Tao Zeng, Yuanyuan Wang, Fangzhi Xu, Lingyi Xiong, Xia Gong, Jingyuan Wan.  (2019)  Geniposide protected hepatocytes from acetaminophen hepatotoxicity by down-regulating CYP 2E1 expression and inhibiting TLR 4/NF-κB signaling pathway.  INTERNATIONAL IMMUNOPHARMACOLOGY,      [PMID:31302451] [10.1016/j.intimp.2019.05.010]

11. Guixin Wu, Min Wen, Lin Sun, Huitao Li, Yubei Liu, Rui Li, Feihua Wu, Rong Yang, Yining Lin.  (2018)  Mechanistic insights into geniposide regulation of bile salt export pump (BSEP) expression.  RSC Advances,  8  (65): (37117-37128).  [PMID:35557817] [10.1039/C8RA06345A]

12. Wenhao Xu, Jingbo Yu, Wen Feng, Weike Su.  (2016)  Selective Extraction of Gardenia Yellow and Geniposide from Gardenia jasminoides by Mechanochemistry.  MOLECULES,  21  (5): (540).  [PMID:27136513] [10.3390/molecules21050540]

13. Han Yan-lu, Yan Teng-teng, Li Hua-xin, Chen Sha-sha, Zhang Zhen-zhen, Wang Meng-yao, Chen Mei-jie, Chen Yuan-li, Yang Xiao-xiao, Wei Ling-ling, Duan Ya-jun, Zhang Shuang.  (2024)  Geniposide alleviates heart failure with preserved ejection fraction in mice by regulating cardiac oxidative stress via MMP2/SIRT1/GSK3β pathway.  ACTA PHARMACOLOGICA SINICA,      [PMID:39060523] [10.1038/s41401-024-01341-5]

14. Yu Zhang, Fang-Mei Liu, Cun-Yu Li, Xue-Jiao Leng, Yun-Feng Zheng, Guo-Ping Peng.  (2025)  Qingkailing injection induces pseudo-allergic reactions via the MRGPRX2 pathway.  American Journal of Translational Research,  17  (3): (2178).  [PMID:40226010] [10.62347/MFBU4210]

15. Mei Luo, Yuelian Wang, Xiaodong Liu, Lin Liu, Li Zhu, Guo Chen, Qing Ye, Chengshi He, Xujue Xiao, Jike Li.  (2025)  Geniposide Suppresses Tumor Progression Through DUOX1-Mediated Ferroptosis in Hepatocellular Carcinoma.  AMERICAN JOURNAL OF CHINESE MEDICINE,      [PMID:40621626] [10.1142/S0192415X25500600]

16. Zhang Hui-Wen, Wang Jian-Ye, Liu Yan-Yan, Tian Jing-Min, Park Jinbong, Wang Huan-Yun, Xu Ying-Qi.  (2025)  Elucidating the Anti-Atherosclerotic Mechanisms of Sanzi San: An Integrated Approach Using Serum Pharmacochemistry, Network Pharmacology, and Pharmacokinetics.  World Journal of Traditional Chinese Medicine,      [PMID:] [10.4103/wjtcm.wjtcm_49_25]

17. Jinshuang Wang, Qin Ye, Ningxiang Yu, Weiwei Huan, Jingliang Sun, Xiaohua Nie, Xianghe Meng.  (2021)  Preparation of multiresponsive hydrophilic molecularly imprinted microspheres for rapid separation of gardenia yellow and geniposide from gardenia fruit.  FOOD CHEMISTRY,      [PMID:34823938] [10.1016/j.foodchem.2021.131610]

18. Xiaoyun Yang, Qin Guo, Yingying Dong, Huanhuan Wang, Mengya Dang, Yangyang Sun, Yuan Gao, Dong Bai.  (2025)  Glycyrrhiza Protein-Based Nanoparticles Enhance the Oral Bioavailability and Analgesic Efficacy of Paeoniflorin.  International Journal of Nanomedicine,      [PMID:41262311] [10.2147/IJN.S532397]