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H1792

Sigma-Aldrich

Hyperforin (dicyclohexylammonium) salt

Synonym(s):

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:
12352200
PubChem Substance ID:
329815179
NACRES:
NA.25

Assay

≥98% (HPLC)

Quality Level

100

form

powder

storage condition

protect from light

color

white to off-white

solubility

DMSO: ≥10 mg/mL

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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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.

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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