Xanthohumol (HCID 639665)

概要

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 an antiviral agent, a metabolite, an antineoplastic agent, an EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor, an anti-HIV-1 agent and an apoptosis inducer. It is a member of chalcones, a polyphenol and an aromatic ether. It is a conjugate acid of a xanthohumol(1-).

名称と識別子

優先名称: Xanthohumol
IUPAC: (E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
現地名: キサントフモール
英語名: Xanthohumol
分子式: C21H22O5
分子量: 354.4

名称と別名

Xanthohumol6754-58-1Xantho-flav(E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-oneDTXSID00893171T4467YT1NT(2E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-oneCHEBI:663311-(2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one2-Propen-1-one, 1-(2,4-hydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-, (E)-(2E)-1-(2,4-DIHYDROXY-6-METHOXY-3-(3-METHYL-2-BUTEN-1-YL)PHENYL)-3-(4-HYDROXYPHENYL)-2-PROPEN-1-ONE(E)-1-(2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

名称をさらに表示

キサントフモール(E)-1-[2,4-ジヒドロキシ-6-メトキシ-3-(3-メチル-2-ブテニル)フェニル]-3-(4-ヒドロキシフェニル)プロペノン2',4,4'-トリヒドロキシ-6'-メトキシ-3'-プレニルカルコンキサントフモール標準品キサントフモールホップ(HUMULUS LUPULUS)由来1-(2,4-ジヒドロキシ-3-プレニル-6-メトキシフェニル)-3-(4-ヒドロキシフェニル)アクリルアルデヒド1-[2,4-ジヒドロキシ-6-メトキシ-3-(3-メチルブタ-2-エン-1-イル)フェニル]-3-(4-ヒドロキシフェニル)プロパ-2-エン-1-オン2′,4,4′-トリヒドロキシ-3′-プレニル-6′-メトキシカルコンprop-2-en-1-oneXanthohuMoXanthohumol-RMXantho Flav-PureXanthohumol, >99%Xanthohumol 99.8%Xanthohumol StandardXanthohumol (6CI, 7CI)

XanthoFlav(2E)-1-(2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-oneRefChem:195131DTXCID6013231103'-(3,3-Dimethyl allyl)-2',4',4-trihydroxy-6'-methoxychalcone614-078-4(E/Z)-XanthohumolMFCD00210576

データベース識別子

CAS: 6754-58-1
PubChem CID: 639665
DTXSID: DTXSID00893171
ChEMBL: CHEMBL253896
ChEBI: CHEBI:66331
UNII: T4467YT1NT
EC Number: 614-078-4
Nikkaji: J1.438.271B、J17.881K

物性

構造計算による物性

XLogP: 5.1
極性表面積: 87 Å²
水素結合供与体数: 3
水素結合受容体数: 5
回転可能結合数: 6
重原子数: 26
形式電荷: 0
複雑度: 514

実験および物理化学的性質

LipidsPolyketides [PK] -> Flavonoids [PK12] -> Chalcones and dihydrochalcones [PK1212]

Melting Point172 °C

Physical DescriptionSolid

物理化学的性質

融点: 157 · 157-159℃
沸点: 576.5 · 576.5±50.0 °C(Predicted)
比重(密度): 1.244 · 1.244
貯蔵温度: 2 · 2-8°C
溶解性: 10 mg/mL · エタノール：可溶10mg/mL
外見: 粉
酸解離定数(Pka): 7.59 · 7.59±0.45(Predicted)
色: 黄色
由来生物: plant (Humulus lupulus)
安定性: -20 °Cで最大1か月保存できます。 · DMSO溶液またはエタノール溶液で-20°Cで最大1か月保存できます。
化粧品成分の機能: スキンコンディショニング
InChI: InChI=1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+
InChIKey: ORXQGKIUCDPEAJ-YRNVUSSQSA-N
SMILES: C(C1=C(OC)C=C(O)C(C/C=C(/C)\C)=C1O)(=O)/C=C/C1=CC=C(O)C=C1
LogP: 5.172 · 5.172 (est)

化学的性質 · 1 件

化学的特性Xanthohumol is a Light yellow to Brown powder to crystal. It can dissolve in ethanol. This compound is a natural prenylated chalcone isolated from the hop plant, H. lupulus. Xanthohumol and its metabolites induce protective detoxification enzymes, at least in part via the nuclear factor erythroid-2-related factor 2 pathway.

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 4.2% (4 of 96) of reports.

Warning

H317 (95.8%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 96 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Hazard Classes and CategoriesSkin Sens. 1 (95.8%)

安全データ

wgk: 3
rtecs: UD5574117
ridadr: UN 3077 9/PG 3
hs_code: 29145090
risk_code: 50/53-43
hazard_code: N,Xi
safety_code: 60-61-45-22
ストレージクラス: 11 - Combustible Solids

化学と産業

薬理情報

MeSH Pharmacological Classification · 2 件

Substances that inhibit or prevent the proliferation of NEOPLASMS.

Agents and endogenous substances that antagonize or inhibit the development of new blood vessels.

Cellular LocationsMembrane

応用分野 · 3 件

説明Xanthohumol(XH, 6754-58-1) binds to the N-terminal domain of valosin-containing protein (VCP), an essential protein for autophagosome maturation. Xanthohumol inhibits the function of VCP thereby impairing autophagosome maturation and resulting in accumulation of the microtubule-associated protein 1 light chain 3-II (LC3-II) Impairs prostate cancer cell growth and proliferation Cell permeable.

使用Xanthohumol from hop (Humulus lupulus) has been used:to treat glioblastoma cells to test its effect on inducing apoptosisto test its protective effect in renal ischemia/reperfusion (I/R) injuryas a component of Dulbecco′s modified Eagle medium (DMEM) to test its antiviral activity in Huh7.5 cells infected with hepatitis C virus cell culture (HCVcc) system

一般的な説明Xanthohumol (XN), a prenylated chalcone present in Hop (Humulus lupulus), has been found to possess prominent activities against aging, diabetes, inflammation, microbial infection, and cancer.

サプライヤー50 社

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]

山西玉宁生物科技有限公司13623677056

南京普怡生物科技有限公司13814510036 · [email protected]

合肥翰刚医药科技有限公司+8618062405514 · [email protected]

補足説明 · 1 件

定義ChEBI: 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-).

キサントフモール

基本情報

概要