A chromone with diverse biological activities
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Prim-O-Glucosylcimifugin

Item No. 34921

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S)-7-[(β-D-glucopyranosyloxy)methyl]-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-4-methoxy-5H-furo[3,2-g][1]benzopyran-5-one
CAS Number
80681-45-4
Synonyms
  • 1''-O-Glucosylcimifugin
  • PGCN
Molecular Formula
C22H28O11
Formula Weight
468.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 15 mg/mlDMSO: 15 mg/mlEthanol: 15 mg/mlPBS (pH 7.2): 5 mg/ml
λmax
215, 292 nm
SMILES
COC1=C(C[C@@H](C(C)(O)C)O2)C2=CC(OC(CO[C@@H]3O[C@@H]([C@H]([C@@H](O)[C@H]3C)O)CO)=C4)=C1C4=O
InChi Code
InChI=1S/C23H30O10/c1-10-19(26)20(27)16(8-24)33-22(10)30-9-11-5-13(25)18-15(31-11)7-14-12(21(18)29-4)6-17(32-14)23(2,3)28/h5,7,10,16-17,19-20,22,24,26-28H,6,8-9H2,1-4H3/t10-,16-,17+,19+,20-,22-/m1/s1
InChi Key
WSIDVSXNVLGHLR-GOSDGTEKSA-N
Origin
Plant/Cimicifugae rhizoma
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $95

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    10 mg

    $168

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    25 mg

    $370

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    30 mg

    $647

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    Cayman Chemical
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    Product Description

    Prim-O-glucosylcimifugin is a chromone that has been found in Cimicifuga dahurica and has diverse biological activities.1,2,3,4 It inhibits the proliferation of EGF-stimulated MCF-7 breast cancer cells when used at a concentration of 10 µM.1 Prim-O-glucosylcimifugin (15, 50, and 100 µg/ml) reduces LPS-induced increases in the production of nitric oxide (NO), TNF-α, IL-6, and IL-1β in RAW 264.7 macrophages.2 It decreases pulmonary edema in a mouse model of LPS-induced acute lung injury when administered at doses ranging from 2.5 to 10 mg/kg.3 Prim-O-glucosylcimifugin inhibits formalin-induced tonic pain in rats (ED50 = 1.6 mg/animal).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Huyan, C.T.T., Luyen, B.T.T., Khan, G.J., et al. Chemical constituents from Cimicifuga dahurica and their anti-proliferative effects on MCF-7 breast cancer cells. Molecules 23(5), 1083 (2018).

    2. Zhou, J., Sun, Y.-Y., Sun, M.-Y., et al. Prim-O-glucosylcimifugin attenuates lipopolysaccharideinduced inflammatory response in RAW 264.7 macrophages. Pharmacogn. Mag. 13(51), 378-384 (2017).

    3. Chen, N., Wu, Q., Chi, G., et al. Prime-O-glucosylcimifugin attenuates lipopolysaccharide-induced acute lung injury in mice. Int. Immunopharmacol. 16(2), 139-147 (2013).

    4. Wu, L.-Q., Li, Y., Li, Y.-Y., et al. Antinociceptive effects of prim-O-glucosylcimifugin in inflammatory nociception via reducing spinal COX-2. Biomol. Ther. (Seoul) 24(4), 418-425 (2016).