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PHL89225

Hyperforin (stable Dicyclohexylammonium salt)

phyproof® Reference Substance

Synonym(s):

Hyperforin (dicyclohexylammonium) salt, Hyp-DCHA, Hyperforin-DCHA

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About This Item

Empirical Formula (Hill Notation):
C35H52O4·C12H23N
CAS Number:
238074-03-8
Molecular Weight:
718.10
MDL number:
MFCD04000098
UNSPSC Code:
41116107
NACRES:
NA.24

grade

primary reference standard

product line

phyproof® Reference Substance

Assay

≥98.0% (HPLC)

manufacturer/tradename

PhytoLab

application(s)

food and beverages

format

neat

storage temp.

−20°C

SMILES string

C1CCC(CC1)NC2CCCCC2.CC(C)C(=O)[C@@]34C(O)=C(C\C=C(\C)C)C(=O)[C@@](C\C=C(\C)C)(C[C@H](C\C=C(/C)C)[C@@]3(C)CC\C=C(\C)C)C4=O

InChI

1S/C35H52O4.C12H23N/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10;1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h13-15,18,26-27,38H,12,16-17,19-21H2,1-11H3;11-13H,1-10H2/t27-,33+,34+,35-;/m0./s1

InChI key

ZUYCAROZOLUHJY-DNSWOBEMSA-N

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General description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biochem/physiol Actions

Hyperforin is believed to be the primary active constituent responsible for the antidepressant and anxiolytic properties of the extracts of St. John′s wort. It acts as a reuptake inhibitor of monoamines, including serotonin, norepinephrine, dopamine, and of GABA and glutamate by activating the transient receptor potential ion channel TRPC6. It also is an activator of the pregnane X receptor (PXR), which serves as a key regulator of CYP3A4 transcription, a member of the cytochrome (CYP) P450 enzyme system. Recent studies have found it to have neuroprotective effects against Alzheimer′s disease (AD) neuropathology, including the ability to disassemble amyloid-β aggregates in vitro and improve spatial memory in vivo.
Stable salt of hyperforin. Hyperforin is believed to be the primary active constituent responsible for the antidepressant and anxiolytic properties of the extracts of St. John′s wort. It acts as a reuptake inhibitor of monoamines, including serotonin, norepinephrine, dopamine, and of GABA and glutamate by activating the transient receptor potential ion channel TRPC6. Activation of TRPC6 induces the entry of sodium and calcium into the cell which causes inhibition of monoamine reuptake. It also is an activator of the pregnane X receptor (PXR), which serves as a key regulator of CYP3A4 transcription, a member of the cytochrome (CYP) P450 enzyme system. Recent studies have found other neurological effects, effects on inflammation, as well as antibacterial, antitumoral and antiangiogenic effects.

Other Notes

This compound is commonly found in plants of the genus: hypericum

Legal Information

phyproof is a registered trademark of PhytoLab GmbH & Co. KG

Signal Word

Danger

Hazard Statements

H302,H314,H400

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Eye Dam. 1 - Skin Corr. 1B

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
117212
125666639
66069095

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Chengkang He et al.
Clinical and translational medicine, 10(6), e205-e205 (2020-11-03)
Recurrent moderate hypoglycemia (RH), a major adverse effect of hypoglycemic therapy in diabetic patients, is one of the main risk factors for cognitive impairment and dementia. Transient receptor potential canonical channel 6 (TRPC6) is a potential therapeutic target for Alzheimer's

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