Chrysin

Names
IUPAC name

5,7-Dihydroxyflavone

Systematic IUPAC name

5,7-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one

Other names

NP-005901; Galangin flavanone

Identifiers

CAS Number

* 480-40-0 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:75095 N

ChEMBL |

* ChEMBL117 Y

ChemSpider |

* 4444926 Y

KEGG |

* C10028 Y

PubChem CID

* 5281607

UNII |

* 3CN01F5ZJ5 Y

InChI

* InChI=1S/C15H10O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-8,16-17H Y

Key: RTIXKCRFFJGDFG-UHFFFAOYSA-N Y

* InChI=1/C15H10O4/c16-10-6-11(17)15-12(18)8-13 (19-14(15)7-10)9-4-2-1-3-5-9/h1-8,16-17H

Key: RTIXKCRFFJGDFG-UHFFFAOYAO

SMILES

* O=C\1c3c(O/C(=C/1)c2ccccc2)cc(O)cc3O

Properties

Chemical formula

| C15H10O4
Molar mass | 254.241 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

Chrysin, also called 5,7-dihydroxyflavone,[1] is a flavone found in honey, propolis, the passion flowers, Passiflora caerulea and Passiflora incarnata, and in Oroxylum indicum.[2] It is extracted from various plants, such as the blue passion flower (Passiflora caerulea).[1] Following oral intake by humans, chrysin has low bioavailability and rapid excretion.[1] It is under basic research to evaluate its safety and potential biological effects.[1]

Chrysin is an ingredient in dietary supplements.[3] As of 2016, there was no clinical use of chrysin,[1] and no evidence for its effect on testosterone levels.[4] In 2016, the US Food and Drug Administration did not recommend chrysin be included on the list of bulk drug substances that can be used in compounding under section 503A of the Federal Food, Drug, and Cosmetic Act.[5]

## Contents

* 1 Occurrence
* 2 Bioavailability
* 3 Oral and topical application
* 4 Safety
* 5 Research
* 6 Bibliography
* 7 References

## Occurrence

A component in various medicinal plants (e.g. Scutellaria baicalensis), chrysin is a dihydroxyflavone, a type of flavonoid.[6] It is also found in honey, propolis, the passion flowers, Passiflora caerulea and Passiflora incarnata, in Oroxylum indicum,[2] carrots,[1] chamomile,[7] many fruits, and in mushrooms, such as the mushroom Pleurotus ostreatus.[6] It is extracted from various plants,[1] such as the blue passion flower (Passiflora caerulea).[1]

The amount of chrysin in honey from various plant sources is about 0.2 mg per 100 g.[8] Chrysin is typically found at higher amounts in propolis than in honey.[9] A 2010 study found the amount of chrysin was 0.10 mg/kg in honeydew honey, and 5.3 mg/kg in forest honeys.[10] A 2010 study found the amount of chrysin in propolis was as much as 28 g/L.[10] A 2013 study found the amount of chrysin in various mushrooms from the island of Lesvos, Greece, varied between 0.17 mg/kg in Lactarius deliciosus to 0.34 mg/kg in Suillus bellinii.[10]

## Bioavailability

The effects of chrysin are reliant on its bioavailability and solubility.[10] Following oral intake by humans, chrysin has low bioavailability and rapid excretion.[1] As a result, it is poorly absorbed.[1]

A 1998 study determined that the highest amounts in plasma was from 12 to 64 nM.[10] As of 2015, the serum levels of chrysin have not been cited in the literature.[10] Following oral intake by humans, the bioavailability was reported to be from 0.003% to 0.02%.[10]

## Oral and topical application

There is insufficient information to determine how long chrysin has been used in pharmacy compounding.[11] Chrysin is used as an ingredient in dietary supplements, but there is no information on systemic exposure from topical application.[3] As of 2016, there was no evidence to support any effect of oral chrysin on testosterone levels,[4] or an any disease-modifying activity with oral or topical formulations.[12]

## Safety

A daily consumed amount of chrysin of 0.5 to 3 g is considered safe.[6] As of 2016, there was no toxicity attributable to chrysin in clinical trials or adverse event reporting.[13] As of 2016, clinical safety issues have not been identified.[14] As of 2016, nonclinical data suggest potential concerns.[14] In 2016, the US Food and Drug Administration did not recommend chrysin be included on the list of bulk drug substances that can be used in compounding under section 503A of the Federal Food, Drug, and Cosmetic Act based on consideration of the following criteria: (1) physicochemical characterization; (2) safety; (3) effectiveness; and (4) historical use of the substance in compounding.[5]

## Research

As of 2016, there is no evidence for chrysin being used in human clinical applications.[1] Research showed that orally administered chrysin does not have clinical activity as an aromatase inhibitor.[1][15] Nanoformulations of polyphenols, including chrysin, are made using various carrier methods, such as liposomes and nanocapsules.[16]

## Bibliography

* Brave, Michael (23 June 2016). "Chrysin". Pharmacy Compounding Advisory Committee, Division of Oncology Products, US Food and Drug Administration. pp. 1–13. https://www.fda.gov/downloads/AdvisoryCommittees/CommitteesMeetingMaterials/Drugs/PharmacyCompoundingAdvisoryCommittee/UCM509958.pdf. This article incorporates text from this source, which is in the public domain.

## References

1. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 "Chrysin: Compound Summary for CID 5281607". PubChem, National Center for Biotechnology Information, US National Institutes of Health. 14 July 2018. https://pubchem.ncbi.nlm.nih.gov/compound/chrysin#section=Top.
2. ↑ 2.0 2.1 Morissette, Marc; Litim, Nadhir; Di Paolo, Thérèse (18 May 2017). "Chapter 2 – Natural Phytoestrogens: A Class of Promising Neuroprotective Agents for Parkinson Disease". in Brahmachari, Goutam. Discovery and Development of Neuroprotective Agents from Natural Products. Elsevier Science. pp. 32. doi:10.1016/B978-0-12-809593-5.00002-1. ISBN 978-0-12-809769-4. https://books.google.com/books?id=LzVHDgAAQBAJ&pg=PA32.
3. ↑ 3.0 3.1 FDA 2016, p. 3.
4. ↑ 4.0 4.1 FDA 2016, p. 8.
5. ↑ 5.0 5.1 FDA 2016, p. 13.
6. ↑ 6.0 6.1 6.2 "Protective Effects of Chrysin Against Drugs and Toxic Agents". Dose-response 15 (2): 1559325817711782. 2017. doi:10.1177/1559325817711782. PMID 28694744.
7. ↑ Zhandi, M; Ansari, M; Roknabadi, P; Zare Shahneh, A; Sharafi, M (2017). "Orally administered Chrysin improves post-thawed sperm quality and fertility of rooster". Reproduction in Domestic Animals 52 (6): 1004–1010. doi:10.1111/rda.13014. ISSN 0936-6768. PMID 28695606.
8. ↑ "Extraction of Honey Polyphenols: Method Development and Evidence of Cis Isomerization". Analytical Chemistry Insights 11: 49–57. 2016. doi:10.4137/ACI.S39739. PMID 27547032.
9. ↑ "Review of the anticancer activities of bee products". Asian Pacific Journal of Tropical Biomedicine 4 (5): 337–44. 2014. doi:10.12980/APJTB.4.2014C1262. PMID 25182716.
10. ↑ 10.0 10.1 10.2 10.3 10.4 10.5 10.6 "Neuroprotective effects of chrysin: From chemistry to medicine". Neurochemistry International 90: 224–31. 2015. doi:10.1016/j.neuint.2015.09.006. PMID 26386393.
11. ↑ FDA 2016, p. 11.
12. ↑ FDA 2016, p. 9.
13. ↑ FDA 2016, p. 10.
14. ↑ 14.0 14.1 FDA 2016, p. 12.
15. ↑ "No evidence for the in vivo activity of aromatase-inhibiting flavonoids". The Journal of Steroid Biochemistry and Molecular Biology 78 (3): 231–9. September 2001. doi:10.1016/S0960-0760(01)00098-X. PMID 11595503.
16. ↑ "Polyphenol nanoformulations for cancer therapy: experimental evidence and clinical perspective". International Journal of Nanomedicine 12: 2689–2702. 2017. doi:10.2147/IJN.S131973. PMID 28435252.

* v
* t
* e

Xenobiotic-sensing receptor modulators

CAR|

* Agonists: 6,7-Dimethylesculetin
* Amiodarone
* Artemisinin
* Benfuracarb
* Carbamazepine
* Carvedilol
* Chlorpromazine
* Chrysin
* CITCO
* Clotrimazole
* Cyclophosphamide
* Cypermethrin
* DHEA (prasterone)
* Efavirenz
* Ellagic acid
* Griseofulvin
* Methoxychlor
* Mifepristone
* Nefazodone
* Nevirapine
* Nicardipine
* Octicizer
* Permethrin
* Phenobarbital
* Phenytoin
* Pregnanedione (5β-dihydroprogesterone)
* Reserpine
* TCPOBOP
* Telmisartan
* Tolnaftate
* Troglitazone
* Valproic acid

* Antagonists: 3,17β-Estradiol
* 3α-Androstanol
* 3α-Androstenol
* 3β-Androstanol
* 17-Androstanol
* AITC
* Ethinylestradiol
* Meclizine
* Nigramide J
* Okadaic acid
* PK-11195
* S-07662
* T-0901317

PXR|

* Agonists: 17α-Hydroxypregnenolone
* 17α-Hydroxyprogesterone
* Δ4-Androstenedione
* Δ5-Androstenediol
* Δ5-Androstenedione
* AA-861
* Allopregnanediol
* Allopregnanedione (5α-dihydroprogesterone)
* Allopregnanolone (brexanolone)
* Alpha-Lipoic acid
* Ambrisentan
* AMI-193
* Amlodipine besylate
* Antimycotics
* Artemisinin
* Aurothioglucose
* Bile acids
* Bithionol
* Bosentan
* Bumecaine
* Cafestol
* Cephaloridine
* Cephradine
* Chlorpromazine
* Ciglitazone
* Clindamycin
* Clofenvinfos
* Chloroxine
* Clotrimazole
* Colforsin
* Corticosterone
* Cyclophosphamide
* Cyproterone acetate
* Demecolcine
* Dexamethasone
* DHEA (prasterone)
* DHEA-S (prasterone sulfate)
* Dibunate sodium
* Diclazuril
* Dicloxacillin
* Dimercaprol
* Dinaline
* Docetaxel
* Docusate calcium
* Dodecylbenzenesulfonic acid
* Dronabinol
* Droxidopa
* Eburnamonine
* Ecopipam
* Enzacamene
* Epothilone B
* Erythromycin
* Famprofazone
* Febantel
* Felodipine
* Fenbendazole
* Fentanyl
* Flucloxacillin
* Fluorometholone
* Griseofulvin
* Guggulsterone
* Haloprogin
* Hetacillin potassium
* Hyperforin
* Hypericum perforatum (St John's wort)
* Indinavir sulfate
* Lasalocid sodium
* Levothyroxine
* Linolenic acid
* LOE-908
* Loratadine
* Lovastatin
* Meclizine
* Metacycline
* Methylprednisolone
* Metyrapone
* Mevastatin
* Mifepristone
* Nafcillin
* Nicardipine
* Nicotine
* Nifedipine
* Nilvadipine
* Nisoldipine
* Norelgestromin
* Omeprazole
* Orlistat
* Oxatomide
* Paclitaxel
* Phenobarbital
* Piperine
* Plicamycin
* Prednisolone
* Pregnanediol
* Pregnanedione (5β-dihydroprogesterone)
* Pregnanolone
* Pregnenolone
* Pregnenolone 16α-carbonitrile
* Proadifen
* Progesterone
* Quingestrone
* Reserpine
* Reverse triiodothyronine
* Rifampicin
* Rifaximin
* Rimexolone
* Riodipine
* Ritonavir
* Simvastatin
* Sirolimus
* Spironolactone
* Spiroxatrine
* SR-12813
* Suberoylanilide
* Sulfisoxazole
* Suramin
* Tacrolimus
* Tenylidone
* Terconazole
* Testosterone isocaproate
* Tetracycline
* Thiamylal sodium
* Thiothixene
* Thonzonium bromide
* Tianeptine
* Troglitazone
* Troleandomycin
* Tropanyl 3,5-dimethulbenzoate
* Zafirlukast
* Zeranol

* Antagonists: Ketoconazole
* Sesamin

See also
Receptor/signaling modulators
Nuclear receptor modulators

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*[CAR]: Constitutive androstane receptor
*[PXR]: Pregnane X receptor