AVOBENZONE

First approved in 1988

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H22O3
Molecular Weight	310.3869
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(C=C1)C(=O)CC(=O)C2=CC=C(C=C2)C(C)(C)C

InChI

InChIKey=XNEFYCZVKIDDMS-UHFFFAOYSA-N

InChI=1S/C20H22O3/c1-20(2,3)16-9-5-14(6-10-16)18(21)13-19(22)15-7-11-17(23-4)12-8-15/h5-12H,13H2,1-4H3

HIDE SMILES / InChI

Molecular Formula	C20H22O3
Molecular Weight	310.3869
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021501s003lbl.pdf
Curator's Comment: description was created based on several sources, including: http://www.wikidoc.org/index.php/Avobenzone | https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=de3fd7fb-4a28-4db8-9a4d-d7fdd2e45daf

Avobenzone is an oil soluble ingredient used in sunscreen products to absorb the full spectrum of UVA rays. It helps prevent sunburn. Avobenzone works by absorbing the rays and converting them to energy that is less damaging to the skin.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Sunburn 84 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021501s003lbl.pdf	Preventing		Approved 8583	SHADE UVAGUARD Approved Use helps prevent sunburn; higher SPF gives more sunburn protection; helps provide protection from UVA rays (short and long wavelengths). Launch Date 1992

C_max

Value	Dose	Co-administered	Analyte	Population
7.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31058986/	832.5 mg 4 times / day multiple, topical dose: 832.5 mg route of administration: Topical experiment type: MULTIPLE co-administered: OCTOCRYLENE	OCTOCRYLENE	AVOBENZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31058986/	810 mg 4 times / day multiple, topical dose: 810 mg route of administration: Topical experiment type: MULTIPLE co-administered: OXYBENZONE	OXYBENZONE	AVOBENZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.4 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31058986	810 mg 4 times / day multiple, topical dose: 810 mg route of administration: Topical experiment type: MULTIPLE co-administered: OXYBENZONE	OXYBENZONE	AVOBENZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.8 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31058986	576 mg 4 times / day multiple, topical dose: 576 mg route of administration: Topical experiment type: MULTIPLE co-administered: OCTOCRYLENE	OCTOCRYLENE	AVOBENZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
591.2 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31058986/	832.5 mg 4 times / day multiple, topical dose: 832.5 mg route of administration: Topical experiment type: MULTIPLE co-administered: OCTOCRYLENE	OCTOCRYLENE	AVOBENZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
350.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31058986/	810 mg 4 times / day multiple, topical dose: 810 mg route of administration: Topical experiment type: MULTIPLE co-administered: OXYBENZONE	OXYBENZONE	AVOBENZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
112.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31058986/	832.5 mg 4 times / day multiple, topical dose: 832.5 mg route of administration: Topical experiment type: MULTIPLE co-administered: OCTOCRYLENE	OCTOCRYLENE	AVOBENZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
94.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31058986/	810 mg 4 times / day multiple, topical dose: 810 mg route of administration: Topical experiment type: MULTIPLE co-administered: OXYBENZONE	OXYBENZONE	AVOBENZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
45.2 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31058986	810 mg 4 times / day multiple, topical dose: 810 mg route of administration: Topical experiment type: MULTIPLE co-administered: OXYBENZONE	OXYBENZONE	AVOBENZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
33 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31058986	576 mg 4 times / day multiple, topical dose: 576 mg route of administration: Topical experiment type: MULTIPLE co-administered: OCTOCRYLENE	OCTOCRYLENE	AVOBENZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
3.7 g 1.3 times / day multiple, topical Recommended Dose: 3.7 g, 1.3 times / day Route: topical Route: multiple Dose: 3.7 g, 1.3 times / day Sources: https://www.fda.gov/media/71361/download	healthy, 3.69 years (range: 0.64-48.15 years) Health Status: healthy Age Group: 3.69 years (range: 0.64-48.15 years) Sex: M+F Sources: https://www.fda.gov/media/71361/download	Other AEs: Dermatitis, Eczema... Other AEs: Dermatitis (2.5%) Eczema (1.3%) Sources: https://www.fda.gov/media/71361/download
1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: https://www.fda.gov/media/71361/download	healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: https://www.fda.gov/media/71361/download	Other AEs: Acne, Dermatitis... Other AEs: Acne (4.8%) Dermatitis (2.8%) Dry skin (1.2%) Eczema (1.2%) Erythema (1.2%) Pruritus (2%) Rosacea (0.4%) Seborrhea (0.8%) Skin discomfort (1.2%) Sunburn (0.8%) Conjunctivitis (0.8%) Taste perversion (0.4%) Sources: https://www.fda.gov/media/71361/download
3.1 g 1.2 times / day multiple, topical Recommended Dose: 3.1 g, 1.2 times / day Route: topical Route: multiple Dose: 3.1 g, 1.2 times / day Sources: https://www.fda.gov/media/71361/download	healthy, 6.69 years (range: 0.5-67.95 years) Health Status: healthy Age Group: 6.69 years (range: 0.5-67.95 years) Sex: M+F Sources: https://www.fda.gov/media/71361/download	Other AEs: Dermatitis, Eczema... Other AEs: Dermatitis (2.8%) Eczema (0.4%) Erythema (0.8%) Skin discomfort (0.8%) Sunburn (1.6%) Conjunctivitis (0.4%) Sources: https://www.fda.gov/media/71361/download

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as perpetrator

Target	Modality	Activity
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/31530197/	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/31530197/	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/31530197/	no

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B5-01495	http://www.3bsc.com/index/pro_info.php?id=69114
AA Blocks	AA00342H	http://www.aablocks.com/goods/Goods/detail?id=AA00342H
Aaron Chemicals	AR0034U9	http://www.aaronchem.com/70356-09-1
abcr GmbH	AB261323	http://www.abcr.com/shop/en/AB261323
AbMole Bioscience	M5434	http://www.abmole.com/products/avobenzone.html
Acadechem	ACDS-036868	http://www.acadechemical.com/product/111567
Achemica	ACMC-209oe7	http://www.achemica.com/prodinfo/?id=130770
Achemtek	0104-012933	http://www.achemtek.com/70356-09-1
Acorn PharmaTech	ACN-S002307	http://www.acornpharmatech.com/
AK Scientific, Inc. (AKSCI)	71158	http://www.aksci.com/item_detail.php?cat=71158
Angene	AGN-PC-0JKY2S	http://www.angenechemical.com/productshow/AGN-PC-0JKY2S.html
Anward	ANW-35885	http://www.anward.com/pro_result/1413
ApexBio Technology	B2079	http://www.apexbt.com/avobenzone.html
Ark Pharm	AK-48454	http://www.arkpharminc.com/products/70356-09-1.html
Aromsyn	AS04672	http://www.aromsyn.com/product/AS04672.html
Aurora Fine Chemicals LLC	A17.901.658	http://online.aurorafinechemicals.com/info?ID=A17.901.658
Avantor Inc	700004-106	https://us.vwr.com/store/product/21572552/1-4-tert-butylphenyl-3-4-methoxyphenyl-1-3-propanedione
Avantor Inc	700004-108	https://us.vwr.com/store/product/21572552/1-4-tert-butylphenyl-3-4-methoxyphenyl-1-3-propanedione
Avantor Inc	700004-110	https://us.vwr.com/store/product/21572552/1-4-tert-butylphenyl-3-4-methoxyphenyl-1-3-propanedione
BioCrick	BCC4891	http://www.biocrick.com/Avobenzone-BCC4891.html
BioSynth	Q-200661	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-200661.html
BLD Pharm	BD51410	http://www.bldpharm.com/products/70356-09-1.html
Boerchem	BC215936	http://www.boerchem.com/?product_36612.html
Chem Scene	CS-2356	http://www.chemscene.com/70356-09-1.html
ChemMol	30107627	http://www.chemmol.com/chemmol/30107627.html
ChemMol	44005429	http://www.chemmol.com/chemmol/44005429.html
ChemMol	49408542	http://www.chemmol.com/chemmol/49408542.html
ChemMol	99160632	http://www.chemmol.com/chemmol/99160632.html
Chemspace	CSSB00016988247	https://chem-space.com/CSSB00016988247
Clearsynth	CS-O-10849	https://www.clearsynth.com/en/CSO10849.html
DC Chemicals	DCAPI1313	http://www.dcchemicals.com//product_show-Avobenzone_Parsol_1789_.html
eNovation Chemicals	D669289	https://www.enovationchem.com/ProductDetails.asp?ProductID=D669289
Finetech	FT-0623334	http://www.finetechnology-ind.com/prod/detail/pub/70356-09-1.html
Hairui	HR129959	http://www.hairuichem.com/en/product/70356-09-1.html
iChemical	EBD34539	http://www.ichemical.com/products/70356-09-1.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00193793	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00193793
LGC Standards	DRE-C15894520	https://www.lgcstandards.com/US/en/p/DRE-C15894520
LGC Standards	LGCFOR0902.00	https://www.lgcstandards.com/US/en/p/LGCFOR0902.00
MedChem Express	HY-B0316	https://www.medchemexpress.com/Avobenzone.html
MuseChem	A000883	https://www.musechem.com/product/A000883.html
Parchem	25912	http://www.parchem.com/chemical-supplier-distributor/Avobenzone-015912.aspx
Renno Tech	RL04694	http://www.rennotech.com/product_show.asp?id=4943
Sigma-Aldrich	1045337_USP	https://www.sigmaaldrich.com/catalog/product/usp/1045337?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	16633_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/16633?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	PHR1073_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/phr1073?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S021211	http://www.sinfoobiotech.com/product/1024609
Smolecule	S519867	http://www.smolecule.com/products/s519867
TCI (Tokyo Chemical Industry)	B3382	http://www.tcichemicals.com/eshop/en/us/commodity/B3382/index.html
THE BioTek	bt-261258	https://www.thebiotek.com/product/inhibitors/bt-261258
VladaChem	VL273859-100G	https://www.vladachem.com/product.php?products=70356-09-1
Yuhao Chemical	LT1520	http://www.chemyuhao.com/70356-09-1.html

PubMed

Title	Date	PubMed
Multiple chemical sensitivities, including iatrogenic allergic contact dermatitis, in a patient with chronic actinic dermatitis: implications for management.	1996 Sep	8957333
Photochemical studies of 4-tert-butyl-4'-methoxydibenzoylmethane (BM-DBM).	2001 Nov 15	11744398
Photostabilization of butyl methoxydibenzoylmethane (Avobenzone) and ethylhexyl methoxycinnamate by bis-ethylhexyloxyphenol methoxyphenyl triazine (Tinosorb S), a new UV broadband filter.	2001 Sep	11594052
The effect of UV absorbing sunscreens on the reflectance and the consequent protection of skin.	2002 Feb	11883599
A new model using liposomes that allow to distinguish between absorption and oxidative properties of sunscreens.	2002 Jan	11837322
The effects of derivatives of the nitroxide tempol on UVA-mediated in vitro lipid and protein oxidation.	2002 Jul 1	12086690
Protection against UVB irradiation by natural filters extracted from lichens.	2002 Nov	12468208
Non-invasive in vivo determination of UVA efficacy of sunscreens using diffuse reflectance spectroscopy.	2003 Aug	12925190
Bioconvertible vitamin antioxidants improve sunscreen photoprotection against UV-induced reactive oxygen species.	2003 Nov-Dec	14730375
Lack of in vitro protection by a common sunscreen ingredient on UVA-induced cytotoxicity in keratinocytes.	2004 Oct 15	15363592
Determination of sixteen UV filters in suncare formulations by high-performance liquid chromatography.	2004 Sep 17	15499924
Photochemical behavior of a new long-chain UV absorber derived from 4-tert-butyl-4'-methoxydibenzoylmethane.	2004 Sep-Oct	15362951
Interaction of polycyclic musks and UV filters with the estrogen receptor (ER), androgen receptor (AR), and progesterone receptor (PR) in reporter gene bioassays.	2005 Feb	15537743
Sunscreen penetration of human skin and related keratinocyte toxicity after topical application.	2005 Jul-Aug	15908756
A new long-chain UV absorber derived from 4-tert-butyl-4'-methoxydibenzoylmethane: absorbance stability under solar irradiation.	2005 Mar-Apr	15870853
Unexpected photolysis of the sunscreen octinoxate in the presence of the sunscreen avobenzone.	2005 Mar-Apr	15560736
Sun protection strength of a hydroquinone 4%/retinol 0.3% preparation containing sunscreens.	2006 Apr	16673798
Evaluation of the photostability of different UV filter combinations in a sunscreen.	2006 Jan 13	16289662
Changes in ultraviolet absorbance and hence in protective efficacy against lipid peroxidation of organic sunscreens after UVA irradiation.	2006 Mar 1	16442301
Design of a photostabilizer having built-in antioxidant functionality and its utility in obtaining broad-spectrum sunscreen formulations.	2006 May-Jun	16492073
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Interactions between different solar UVB/UVA filters contained in commercial suncreams and consequent loss of UV protection.	2006 Sep	17047836
The FDA approves new over-the-counter sunscreen.	2006 Sep-Oct	17326301
[Simultaneous determination of 9 ultraviolet absorbers in cosmetics by high-performance liquid chromatography].	2007	18220048
I've heard there's a new sunscreen that's supposed to offer better skin protection. Can you tell me more?	2007 Jun	17476186
A new sunscreen agent.	2007 May 21	17505409
Transient enol isomers of dibenzoylmethane and avobenzone as efficient hydrogen donors toward a nitroxide pre-fluorescent probe.	2007 May-Jun	17094718
Degradation kinetics of butylmethoxydibenzoylmethane (avobenzone) in aqueous solution.	2007 Oct	18236778
Photostability and efficacy studies of topical formulations containing UV-filters combination and vitamins A, C and E.	2007 Oct 1	17614223
Mexoryl: a review of an ultraviolet a filter.	2007 Sep 15	17805138
OTC product: Anthelios SX.	2007 Sep-Oct	17848358
In vitro assessments of UVA protection by popular sunscreens available in the United States.	2008 Dec	18835064
Influence of hydroxypropyl-beta-cyclodextrin on transdermal penetration and photostability of avobenzone.	2008 Jun	18226883
Assessing retinol stability in a hydroquinone 4%/retinol 0.3% cream in the presence of antioxidants and sunscreen under simulated-use conditions: a pilot study.	2008 Mar	18405792
Evaluation of spray congealing as technique for the preparation of highly loaded solid lipid microparticles containing the sunscreen agent, avobenzone.	2009 Aug	19067396
Optical and electron paramagnetic resonance studies of the excited states of 4-tert-butyl-4'-methoxydibenzoylmethane and 4-tert-butyl-4'-methoxydibenzoylpropane.	2009 Dec 3	19886613
A blocked diketo form of avobenzone: photostability, photosensitizing properties and triplet quenching by a triazine-derived UVB-filter.	2009 Jan-Feb	18673327
Addressing technical challenges associated with the FDA's proposed rules for the UVA in vitro testing procedure.	2009 Nov-Dec	20038348
Filter-filter interactions. Photostabilization, triplet quenching and reactivity with singlet oxygen.	2010 Apr	20354650
Characterization of the UVA protection provided by avobenzone, zinc oxide, and titanium dioxide in broad-spectrum sunscreen products.	2010 Dec 1	20806994
Polymorphism and reversible mechanochromic luminescence for solid-state difluoroboron avobenzone.	2010 Feb 24	20108897
True photoallergy to sunscreens is rare despite popular belief.	2010 Jul-Aug	20646669
A randomized, controlled comparative study of the wrinkle reduction benefits of a cosmetic niacinamide/peptide/retinyl propionate product regimen vs. a prescription 0.02% tretinoin product regimen.	2010 Mar	20374604
An Assessment of the Efficacy and Safety of CROSS Technique with 100% TCA in the Management of Ice Pick Acne Scars.	2010 May	21031068
Determination of organic UV filters in water by stir bar sorptive extraction and direct analysis in real-time mass spectrometry.	2010 May	20127322
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.	2013 Sep 5	23769903
Chemical allergens stimulate human epidermal keratinocytes to produce lymphangiogenic vascular endothelial growth factor.	2015 Mar 1	25617811

Patents

Sample Use Guides

In Vivo Use Guide

apply liberally 15 min before sun exposure. reapply as needed or after towel drying, 40 min of swimming, or perspiring.

Route of Administration: Topical

In Vitro Use Guide

Avobenzone 2% and ethyl ascorbic acid2% represented the best photostability with avobenzone concentrations decrease by 11,82% for 15 hour using UVA lamp irradiation 4,7 mW/cm2.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:56:01 GMT 2025` Edited by `admin` on `Mon Mar 31 17:56:01 GMT 2025`
Record UNII	G63QQF2NOX
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BUTYL METHOXYDIBENZOYLMETHANE

Preferred Name

English

AVOBENZONE

Official Name

English

NEOHELIOPAN 357

Brand Name

English

AVOBENZONE [USP-RS]

Common Name

English

Avobenzone [WHO-DD]

Common Name

English

NSC-758680

Code

English

1,3-PROPANEDIONE, 1-(4-(1,1-DIMETHYLETHYL)PHENYL)-3-(4-METHOXYPHENYL)-

Systematic Name

English

ESCALOL 517

Brand Name

English

4-METHOXY-4'-TERT-BUTYLDIBENZOYLMETHANE

Common Name

English

1-(4-TERT-BUTYLPHENYL)-3-(4-METHOXYPHENYL)PROPAN-1,3-DIONE

Systematic Name

English

AVOBENZONE [MART.]

Common Name

English

AVOBENZONE [USP IMPURITY]

Common Name

English

AVOBENZONE [MI]

Common Name

English

AVOBENZONE [HSDB]

Common Name

English

CAPITAL SOLEIL COMPONENT AVOBENZONE

Common Name

English

ANTHELIOS SX COMPONENT AVOBENZONE

Common Name

English

avobenzone [INN]

Common Name

English

EUSOLEX 9020

Brand Name

English

AVOBENZONE [ORANGE BOOK]

Common Name

English

AVOBENZONE [USP MONOGRAPH]

Common Name

English

AVOBENZONE [USAN]

Common Name

English

PARSOL 1789

Brand Name

English

SHADE UVAGUARD COMPONENT AVOBENZONE

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

142401