(R)-Humulone

Modify Date: 2024-01-02 18:42:46

(R)-Humulone structure	Common Name	(R)-Humulone
	CAS Number	26472-41-3	Molecular Weight	362.460
	Density	1.2±0.1 g/cm3	Boiling Point	571.4±50.0 °C at 760 mmHg
	Molecular Formula	C₂₁H₃₀O₅	Melting Point	65-66.5℃
	MSDS	N/A	Flash Point	313.4±26.6 °C

Use of (R)-Humulone

Humulone (α-Lupulic acid), a prenylated phloroglucinol derivative, is a potent cyclooxygenase-2 (COX-2) inhibitor. Humulone acts as a positive modulator of GABAA receptor at low micromolar concentrations. Humulone is an inhibitor of bone resorption. Humulone possesses antioxidant, anti-angiogenic and apoptosis-inducing properties[1][2][3].

Name	(6S)-3,5,6-trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
Synonym	More Synonyms

Description	Humulone (α-Lupulic acid), a prenylated phloroglucinol derivative, is a potent cyclooxygenase-2 (COX-2) inhibitor. Humulone acts as a positive modulator of GABAA receptor at low micromolar concentrations. Humulone is an inhibitor of bone resorption. Humulone possesses antioxidant, anti-angiogenic and apoptosis-inducing properties[1][2][3].
Related Catalog	Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cardiovascular Disease Signaling Pathways >> Immunology/Inflammation >> COX Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor Signaling Pathways >> Neuronal Signaling >> GABA Receptor
Target	COX-2
In Vitro	Humulone (0.1, 1, 10, 100, 1000, 10000 nM; for 12 h) with with 10 ng/ml TNFα dose-dependently decreases the amount of released PGE2 with an IC50 of about 30 nM in MC3T3-E1 cells. Humulone reduces cyclooxygenase activity of the TNFK-treated cells[1]. Humulone (0.1-10000 nM; for 12 h) suppresses the TNFα-induced increase of cyclooxygenase-2 mRNA[1]. Humulone hardly affects the cyclooxygenase-1 activity below 10 μM, whereas inhibits the cyclooxygenase-2 activity with an IC50 of about 1.6 μM in MC3T3-E1 cells[1].
In Vivo	Humulone (10 or 20 mg/kg; IP; single dose) shortens sleep onset and increases the duration of sleep induced by pentobarbital and decreases the spontaneous locomotion in open field at 20 mg/kg[2]. Humulone (10 μmol; applied topically to the dorsal shaved area) pre-treatment significantly inhibited TPA (10 nmol)-induced COX-2 expression in Female ICR mice (6-7 weeks of age) skin[3]. Humulone (1, 10 μmol; applied topical; pre-treatment 30 min) suppresses TPA-induced NF-κB DNA binding. Humulone attenuates TPA-stimulated nuclear translocation of p65 and p50 subunit proteins of NF-κB[3]. Animal Model: Male BALB/cAnNRj mice (9-11 weeks of age)[2] Dosage: 10 or 20 mg/kg Administration: IP; pre-treatment before sodium pentobarbital (35 mg/kg; i.p.) and ethanol (3.5 g/kg) Result: Significantly decreased the latency and prolonged the duration of sleep induced by pentobarbital at 20 mg/kg dose. These effects were not observed at a lower dose of 10 mg/kg. Showed no effect on the onset of sleep induced by ethanol, but significantly increased sleep duration dose-dependently.
References	[1]. K Yamamoto, et al. Suppression of cyclooxygenase-2 gene transcription by humulon of beer hop extract studied with reference to glucocorticoid. FEBS Lett. 2000 Jan 14;465(2-3):103-6. [2]. Ali Y Benkherouf, et al. Humulone Modulation of GABA A Receptors and Its Role in Hops Sleep-Promoting Activity. Front Neurosci. 2020 Oct 14;14:594708. [3]. Jung-Chul Lee, et al. Humulone inhibits phorbol ester-induced COX-2 expression in mouse skin by blocking activation of NF-kappaB and AP-1: IkappaB kinase and c-Jun-N-terminal kinase as respective potential upstream targets. Carcinogenesis. 2007 Jul;28(7):1491-8.

Density	1.2±0.1 g/cm3
Boiling Point	571.4±50.0 °C at 760 mmHg
Melting Point	65-66.5℃
Molecular Formula	C₂₁H₃₀O₅
Molecular Weight	362.460
Flash Point	313.4±26.6 °C
Exact Mass	362.209320
PSA	94.83000
LogP	5.14
Vapour Pressure	0.0±3.6 mmHg at 25°C
Index of Refraction	1.558

Hazard Codes	Xi
WGK Germany	3

N/A

CAS#:125137-35-1

(R)-Humulone

CAS#:26472-41-3

Literature: Carroll, Brian J.; Darland, Gary; Desai, Anuradha; Konda, Veera; Dahlberg, Clinton J.; Urban, Jan Patent: US2012/108671 A1, 2012 ; Location in patent: Page/Page column 18 ;

3-methyl-1-[2,4...

CAS#:4374-93-0

(R)-Humulone

CAS#:26472-41-3

Literature: Carroll, Brian J.; Darland, Gary; Desai, Anuradha; Konda, Veera; Dahlberg, Clinton J.; Urban, Jan Patent: US2012/108671 A1, 2012 ;

Precursor 1
CAS#:4374-93-0 3-methyl-1-[2,4...
DownStream 4
CAS#:504-85-8 4-methylpent-3-... CAS#:78-84-2 Isobutyraldehyde CAS#:67-64-1 Acetone CAS#:78-78-4 isopentane

a-Bitter Acid

(R)-3,5,6-Trihydroxy-2-isovaleryl-4,6-bis-(3-methyl-but-2-enyl)-cyclohexa-2,4-dienon

2,4-Cyclohexadien-1-one, 3,5,6-trihydroxy-2-isovaleryl-4,6-bis(3-methyl-2-butenyl)-, (R)-(-)-

3,5,6β-Trihydroxy-2-isovaleryl-4,6α-bis(3-methyl-2-butenyl)-2,4-cyclohexadienon

Humulon

(6R)-3,5,6-trihydroxy-2-isovaleryl-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dienone

a-Lupulic Acid

2,4-Cyclohexadien-1-one, 3,5,6-trihydroxy-4,6-bis(3-methyl-2-buten-1-yl)-2-(3-methyl-1-oxobutyl)-, (6R)-

2,4-Cyclohexadien-1-one, 3,5,6-trihydroxy-4,6-bis(3-methyl-2-butenyl)-2-(3-methyl-1-oxobutyl)-, (R)-

(R)-2.3.6-Trihydroxy-1.3-bis-(3-methyl-buten-(2)-yl)-5-isovaleryl-cyclohexadien-(1.5)-on-(4)

α-Lupulic acid

(R)-3,5,6-trihydroxy-2-isovaleryl-4,6-bis-(3-methyl-but-2-enyl)-cyclohexa-2,4-dienone

(6R)-3,5,6-Trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methyl-2-buten-1-yl)-2,4-cyclohexadien-1-one

Humulone,mixture of homologues

|A-Lupulic acid

2',3'-Dihydro-3'β,4',6'-trihydroxy-3'α,5'-bis(3-methyl-2-butenyl)-2'-oxoisovalerophenon

(R)-3,5,6-Trihydroxy-4,6-bis(3-methyl-2-butenyl)-2-(3-methyl-1-oxobutyl)-2,4-cyclohexadien-1-one

(6R)-3,5,6-Trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one

|A-Bitter acid

Humulone

humulone, (R)-

α-Bitter acid

Shanghai Jizhi Biochemical Technology Co., Ltd
China
Product Name: (R)-Humulone
Price: ￥1768.0/10mg
Purity: 98.0%
Stocking Period: 2 Day
Contact: Liu jia

DC Chemicals Limited
China
Product Name: Humulone
Price: ￥Inquiry/1g
Purity: 98.9%
Stocking Period: 1 Day
Contact: Tony Cao

Dayang Chem (Hangzhou) Co., Ltd.
China
Product Name: HUMULONE*
Price: $Inquiry/100g $Inquiry/1kg $Inquiry/100kg $Inquiry/1000kg
Purity: 98.0%
Stocking Period: Inquiry
Contact: Ms Wang

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