Xanthohumol from hop (Humulus lupulus)
Xanthohumol
CAS: 6754-58-1
Molecular Formula: C21H22O5
Xanthohumol from hop (Humulus lupulus) - Names and Identifiers
| Name | Xanthohumol |
| Synonyms | XanthohuMo XANTHOHUMOL Xanthohumol XANTHOHUMOL, HUMULUS LU PULUS Xanthohumol from hop (Humulus lupulus) 2',4',4-TRIHYDROXY-6'-METHOXY-3'-PRENYLCHALCONE 1-(2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (2E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one 2-Propen-1-one,1-[2,4-dihydroxy-6-Methoxy-3-(3-Methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-,(2E)- |
| CAS | 6754-58-1 |
| EINECS | 614-078-4 |
| InChIKey | ORXQGKIUCDPEAJ-YRNVUSSQSA-N |
Xanthohumol from hop (Humulus lupulus) - Physico-chemical Properties
| Molecular Formula | C21H22O5 |
| Molar Mass | 354.4 |
| Density | 1.244 |
| Melting Point | 157-159℃ |
| Boling Point | 576.5±50.0 °C(Predicted) |
| Solubility | Soluble in DMSO |
| Appearance | Orange powder |
| Color | Yellow |
| pKa | 7.59±0.45(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month. |
| MDL | MFCD00210576 |
| Physical and Chemical Properties | Character: light yellow crystal extraction Source: antioxidant substances extracted from hops A substance called xanthohumol in hops has attracted more and more attention, this substance belongs to isopentene flavonoid compound (xantho-humol, xn for short), and the research of scientists shows that Xanthohumol has obvious anti-cancer effect. Professor Fang Jianguo, State Key Laboratory of functional organic molecular chemistry, Lanzhou University, found that an active molecule contained in beer called xanthohumol could help the brain fight Parkinson's disease and Alzheimer's disease the violation of neurodegenerative diseases, become the focus and hot spot of the world's major media reports in early 2015. |
| In vitro study | In the culture medium of mouse hepatoma cells, Xanthohumol inhibited Cyp1A activity and induced QR activity. Xanthohumol scavenges reactive oxygen species and inhibits superoxide anion groups and nitric oxide production. In addition, Xanthohumol prevents carcinogenesis by inhibiting DNA synthesis and inducing S-phase cell cycle arrest, apoptosis, and cell differentiation. Xanthohumol exhibits potent anti-HIV-1 activity. |
| In vivo study | In CETP-Tg mice, xanthohumol (p.o.) prevents atherosclerosis resulting from cholesterol accumulation. In TRAMP mice, Xanthohumol (p.o.) induces a decrease in the mean weight of the urogenital (UG) tract, delays advanced tumor progression, and inhibits the growth of poorly differentiated prostate cancer. |
Xanthohumol from hop (Humulus lupulus) - Risk and Safety
| Risk Codes | R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R43 - May cause sensitization by skin contact |
| Safety Description | S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S22 - Do not breathe dust. |
| UN IDs | UN 3077 9/PG 3 |
| WGK Germany | 3 |
| RTECS | UD5574117 |
| HS Code | 29145090 |
Xanthohumol from hop (Humulus lupulus) - Reference Information
| biological activity | xanthahumol, an isopentenylated chalcone from hops that inhibits COX-1 and COX-2 activity, and showed a chemopreventive effect. Xanthochumol can inhibit diacylglycine acyltransferase 1 (DGAT1) and DGAT2, corresponding to an IC50 value of 40 μm. Xanthochumol is also a potent anti-Virus agent against a range of DNA and RNA Virus. Xanthochumol can induce growth arrest and apoptosis in tumor cells. Phase 1. |
| Target | Value |
| COX-1 () | |
| COX-2 () | |
| DGAT1 (Cell-free assay) | 40 μM |
| DGAT2 (Cell-free assay) | 40 μM |
| Use | standard for analysis of herbal products. for content determination/identification/pharmacological experiments, etc |
Last Update：2024-04-09 19:05:13
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View History
Xanthohumol from hop (Humulus lupulus)
Pentanedioic acid, 1,5-bis(2-(2-(2-butoxyethoxy)ethoxy)ethyl) ester
3-[[2-(乙酰氧基)乙基][4-[[2-(甲磺酰基)-4-硝基苯基]偶氮]苯基]氨基]丙腈
C.I.Pigment Red 268
[(4-溴苯基)氨基甲酰基]膦酸二丙酯
2-[5-[(3-甲基-2-丁烯-1-基)氧基]-2-[3-[4-[(3-甲基-2-丁烯-1-基)氧基]苯基]-1-氧代-2-丙烯-1-基]苯氧基]乙酸
LACTOSYL CERAMIDE
3-[(2,7-Dimethoxyacridin-9-yl)thio]propan-1-amine dihydrochloride
{[(2R)-2-ethylhexyl]oxy}{[(2S)-2-ethylhexyl]oxy}[(trichloromethyl)disulfanyl]phosphane sulfide
Methanone, (3,4-difluorophenyl)[3-(4-morpholinylmethyl)phenyl]-
Pentanedioic acid, 1,5-bis(2-(2-(2-butoxyethoxy)ethoxy)ethyl) ester
3-[[2-(乙酰氧基)乙基][4-[[2-(甲磺酰基)-4-硝基苯基]偶氮]苯基]氨基]丙腈
C.I.Pigment Red 268
[(4-溴苯基)氨基甲酰基]膦酸二丙酯
2-[5-[(3-甲基-2-丁烯-1-基)氧基]-2-[3-[4-[(3-甲基-2-丁烯-1-基)氧基]苯基]-1-氧代-2-丙烯-1-基]苯氧基]乙酸
LACTOSYL CERAMIDE
3-[(2,7-Dimethoxyacridin-9-yl)thio]propan-1-amine dihydrochloride
{[(2R)-2-ethylhexyl]oxy}{[(2S)-2-ethylhexyl]oxy}[(trichloromethyl)disulfanyl]phosphane sulfide
Methanone, (3,4-difluorophenyl)[3-(4-morpholinylmethyl)phenyl]-