Xanthohumol
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Xanthohumol
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CAS No:
6754-58-1
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Formula:
C21H22O5
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Chemical Name:
Xanthohumol
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Synonyms:
2-Propen-1-one,1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-,(2E)-;Xanthohumol;2-Propen-1-one,1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-,(E)-;2-Propen-1-one,1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-,(2E)-;(2E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one;Xantho-Flav;Xantho Flav-Pure;Xanthopure
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CAS No:
Description
Xanthohumol is one of the principal flavonoids isolated from hops, the inhibitor of diacylglycerol acetyltransferase (DGAT), COX-1 and COX-2, and shows anti-cancer and anti-angiogenic activities.
Solid
Xanthohumol is a member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4', a methoxy group at position 6' and a prenyl group at position 3'. Isolated from Humulus lupulus, it induces apoptosis in human malignant glioblastoma cells. It has a role as a metabolite, an apoptosis inducer, an antineoplastic agent, an antiviral agent, an EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor and an anti-HIV-1 agent. It is a member of chalcones, a polyphenol and an aromatic ether. It is a conjugate acid of a xanthohumol(1-).|Xanthohumol is under investigation in clinical trial NCT01367431 (Xanthohumol and Metabolic Syndrome).|Xanthohumol is a prenylated flavonoid derived from the female flowers of the hops plant (Humulus lupulus L), with potential chemopreventive and antineoplastic activities. Upon administration, xanthohumol scavenges reactive oxygen species (ROS), thereby preventing DNA damage due to oxidative stress. In addition, xanthohumol is able to increase the expression of phase II cytoprotective enzymes, thereby inactivating carcinogens. This agent exerts anti-inflammatory activity, through the inhibition of inflammation-inducing enzymes, inhibits DNA synthesis, and induces apoptosis of susceptible cancer cells. Xanthohumol also decreases the expression of C-X-C chemokine receptor 4 (CXCR4), thereby preventing cancer cell invasion.
Characteristics
87
5.1
Solid
1.2±0.1 g/cm3
172 °C
576.5ºC at 760 mmHg
203.4±23.6 °C
1.641
ethanol: soluble10mg/mL
2-8°C
Safety Information
UN30779/PG3
3
50/53-43
60-61-45-22
UD5574117
N,Xi
P273-P280
H317-H400
|Warning|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P273, P280, P302+P352, P321, P333+P313, P363, P391, and P501|Aggregated GHS information provided by 42 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Drug Information
Agents and endogenous substances that antagonize or inhibit the development of new blood vessels. (See all compounds classified as Angiogenesis Inhibitors.)|Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)
1-(2,4-dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one
Xanthohumol Use and Manufacturing
Standard for analysis of herbal products.
Polyketides [PK] -> Flavonoids [PK12] -> Chalcones and dihydrochalcones [PK1212]
Computed Properties
Molecular Weight:354.4
XLogP3:5.1
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:6
Exact Mass:354.14672380
Monoisotopic Mass:354.14672380
Topological Polar Surface Area:87
Heavy Atom Count:26
Complexity:515
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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