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Chemistry

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Also known as: 6754-58-1, 569-83-5, Xantho-flav, 1-(2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one, (e)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one, T4467yt1nt
Molecular Formula
C21H22O5
Molecular Weight
354.4  g/mol
InChI Key
ORXQGKIUCDPEAJ-YRNVUSSQSA-N
FDA UNII
T4467YT1NT

Xanthohumol
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.
1 2D Structure

Xanthohumol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
2.1.2 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+
2.1.3 InChI Key
ORXQGKIUCDPEAJ-YRNVUSSQSA-N
2.1.4 Canonical SMILES
CC(=CCC1=C(C(=C(C=C1O)OC)C(=O)C=CC2=CC=C(C=C2)O)O)C
2.1.5 Isomeric SMILES
CC(=CCC1=C(C(=C(C=C1O)OC)C(=O)/C=C/C2=CC=C(C=C2)O)O)C
2.2 Other Identifiers
2.2.1 UNII
T4467YT1NT
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (2e)-1-(2,4-dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one

2. (2e)-3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxy-3-(3-methyl-2-buten-1-yl)phenyl)-2-propen-1-one

3. 1-(2,4-dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one

4. 2,4,4',6-tetrahydroxy-3-(3,3-dimethylallyl)chalcone

5. Desmethylxanthohumol

6. Xantho-flav

7. Xanthoflav

2.3.2 Depositor-Supplied Synonyms

1. 6754-58-1

2. 569-83-5

3. Xantho-flav

4. 1-(2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

5. (e)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

6. T4467yt1nt

7. Chebi:66331

8. Xanthohumol(random Configuration)

9. 2',4,4'-trihydroxy-6'-methoxy-3'-prenylchalcone

10. 1-(2,4-dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one

11. (2e)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

12. (2e)-1-(2,4-dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one

13. (e)-1-(2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

14. (e)-1-(2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

15. 2-propen-1-one, 1-(2,4-hydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-, (e)-

16. Unii-t4467yt1nt

17. Mfcd00210576

18. (2e)-1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one

19. Xanthohumo

20. Xanthohumol From Hop (humulus Lupulus)

21. 2',4,4'-trihydroxy-3'-prenyl-6'-methoxychalcone

22. Xanthohumol [inci]

23. Schembl143683

24. Chembl253896

25. Megxp0_000104

26. Xanthohumol(randomconfiguration)

27. Acon1_001634

28. Chebi:94745

29. Dtxsid00893171

30. Hms3886h19

31. Bcp18498

32. Zinc5158937

33. Bdbm50384998

34. Lmpk12120294

35. S7889

36. Akos016010098

37. Ccg-268086

38. Db15359

39. (e)-1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)propenone

40. Smp2_000278

41. Ncgc00180304-01

42. Ac-31276

43. Bs-17392

44. X0068

45. A867246

46. Q408088

47. Brd-k77390737-001-01-6

48. Q27166535

49. Xanthohumol, Primary Pharmaceutical Reference Standard

50. Xanthohumol From Hop (humulus Lupulus), >=96% (hplc)

51. 1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one

52. 2-propen-1-one, 1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-, (2e)-

2.4 Create Date
2006-01-18
3 Chemical and Physical Properties
Molecular Weight 354.4 g/mol
Molecular Formula C21H22O5
XLogP35.1
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count6
Exact Mass354.14672380 g/mol
Monoisotopic Mass354.14672380 g/mol
Topological Polar Surface Area87 Ų
Heavy Atom Count26
Formal Charge0
Complexity515
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)


Angiogenesis Inhibitors

Agents and endogenous substances that antagonize or inhibit the development of new blood vessels. (See all compounds classified as Angiogenesis Inhibitors.)


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ABOUT THIS PAGE

Xanthohumol Manufacturers

A Xanthohumol manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Xanthohumol, including repackagers and relabelers. The FDA regulates Xanthohumol manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Xanthohumol API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Xanthohumol Suppliers

A Xanthohumol supplier is an individual or a company that provides Xanthohumol active pharmaceutical ingredient (API) or Xanthohumol finished formulations upon request. The Xanthohumol suppliers may include Xanthohumol API manufacturers, exporters, distributors and traders.

Xanthohumol GMP

Xanthohumol Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Xanthohumol GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Xanthohumol GMP manufacturer or Xanthohumol GMP API supplier for your needs.

Xanthohumol CoA

A Xanthohumol CoA (Certificate of Analysis) is a formal document that attests to Xanthohumol's compliance with Xanthohumol specifications and serves as a tool for batch-level quality control.

Xanthohumol CoA mostly includes findings from lab analyses of a specific batch. For each Xanthohumol CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Xanthohumol may be tested according to a variety of international standards, such as European Pharmacopoeia (Xanthohumol EP), Xanthohumol JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Xanthohumol USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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