Identification

Generic Name
Diethylamino hydroxybenzoyl hexyl benzoate
DrugBank Accession Number
DB11269
Background

Diethylamino hydroxybenzoyl hexyl benzoate is a UV filter with high absorption in the UV-A range. Minimizing the overexposure of human skin to ultraviolet radiation that may lead to acute and chronic photodamage, diethylamino hydroxybenzoyl hexyl benzoate is an oil-soluble UV filter that may be incorporated in the oil phase of emulsions 4. Diethylamino hydroxybenzoyl hexyl benzoate was approved in Europe in 2005, and is also marketed in the U.S., South America, Mexico, Japan and Taiwan. It has a chemical structure similar to the classical benxophoenone drug class, and displays good photostability 1. It is used in concentrations up to 10% in sunscreen products, either alone or in combination with other UV absorbers 4.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 397.515
Monoisotopic: 397.225308482
Chemical Formula
C24H31NO4
Synonyms
  • Hexyl 2-(4-(diethylamino)-2-hydroxybenzoyl)benzoate

Pharmacology

Indication

Indicated for use as a sunscreen agent.

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Diethylamino hydroxybenzoyl hexyl benzoate is an organic UV filter that attenuates the exposure of UV radiation on human skin 2. In vitro, topical application of diethylamino hydroxybenzoyl hexyl benzoate exerted an anti-inflammatory effect on inflammation-evoked mouse ears by inhibiting oedema formation 3.

Mechanism of action

Diethylamino hydroxybenzoyl hexyl benzoate absorbs in the UV-A range with the peak at 354 nm 1.

Absorption

Based on the findings of a rat study assessing dermal or percutaneous absorption, only a minor amount of diethylamino hydroxybenzoyl hexyl benzoate will undergo percutaneous absorption and most of the compounds will remain in the upper layers of the stratum corneum 4. In rat and porcine skin, the percutaneous absorption was 0.10 ± 0.12 μg/cm^2 or 0.04 ± 0.05% 4.

Volume of distribution

No pharmacokinetic data.

Protein binding

No pharmacokinetic data.

Metabolism

In steady-state and transient photolysis experiments in vitro, diethylamino hydroxybenzoyl hexyl benzoate may be oxidized by H2O2/UV to form degradation products 2. Like other UV filters, diethylamino hydroxybenzoyl hexyl benzoate may be subject to photodegradation upon absorption of UV radiation, which results in the compound passing from a ground state to either a singlet or triplet excited state 1.

Route of elimination

No pharmacokinetic data.

Half-life

No pharmacokinetic data.

Clearance

No pharmacokinetic data.

Adverse Effects
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Toxicity

In a rat acute oral toxicity study, median LD50 value was reported to be >2000 mg/kg 4. No case of overdose has been reported. Diethylamino hydroxybenzoyl hexyl benzoate was not shown to be mutagenic, clastogenic, or phototoxic in vitro 4. The no observed adverse effect level (NOAEL) 200 mg/kg bw/day for maternal toxicity, and 1000 mg/kg bw/day (highest applied dose) for prenatal developmental toxicity 4.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
No interactions found.

Products

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International/Other Brands
Uvinul A Plus (BASF)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Age 20s ESSENCE COVER PACT WHITE DARK BE-35Diethylamino hydroxybenzoyl hexyl benzoate (0.375 g/12.5g) + Octinoxate (0.875 g/12.5g) + Octocrylene (0.5 g/12.5g) + Titanium dioxide (0.8825 g/12.5g)CreamTopicalAekyung Industrial Co., Ltd.2017-06-022020-01-13US flag
Age 20s ESSENCE COVER PACT WHITE DEEP BE-25Diethylamino hydroxybenzoyl hexyl benzoate (0.375 g/12.5g) + Octinoxate (0.875 g/12.5g) + Octocrylene (0.5 g/12.5g) + Titanium dioxide (0.8825 g/12.5g)CreamTopicalAekyung Industrial Co., Ltd.2017-06-022020-01-13US flag
BRING GREEN Tea Tree CICA Cooling SunDiethylamino hydroxybenzoyl hexyl benzoate (3.5 g/100g) + Bemotrizinol (1.5 g/100g) + Octyl triazone (3.0 g/100g) + Polysilicone-15 (2.0 g/100g)StickTopicalCJ Olive Young Corporation2022-08-01Not applicableUS flag
Calming Days Vegan SunscreenDiethylamino hydroxybenzoyl hexyl benzoate (3 g/100mL) + Bisoctrizole (2 g/100mL) + Iscotrizinol (1.2 g/100mL) + Octyl triazone (2.4 g/100mL)GelTopicalMerci Co.2022-10-18Not applicableUS flag
CC Cream SPF 50Diethylamino hydroxybenzoyl hexyl benzoate (2.6 mg/5000mg) + Octyl triazone (0.26 mg/5000mg) + Titanium dioxide (0.83 mg/5000mg)CreamCutaneous; TopicalFRIDDA DORSCH SL2021-04-07Not applicableUS flag
D-one By Tamdoan Bb LightDiethylamino hydroxybenzoyl hexyl benzoate (2 g/100g) + Adenosine (0.04 g/100g) + Arbutin (2 g/100g) + Octinoxate (7 g/100g) + Octisalate (5 g/100g) + Octocrylene (1 g/100g) + Titanium dioxide (2.54 g/100g) + Zinc oxide (5.99 g/100g)CreamTopicalDran Co.,ltd2016-02-232016-09-05US flag
D-one By Tamdoan Bb MediumDiethylamino hydroxybenzoyl hexyl benzoate (2 g/100g) + Adenosine (0.04 g/100g) + Arbutin (2 g/100g) + Octinoxate (7 g/100g) + Octisalate (5 g/100g) + Octocrylene (1 g/100g) + Titanium dioxide (2.54 g/100g) + Zinc oxide (5.99 g/100g)CreamTopicalDran Co.,ltd2019-11-19Not applicableUS flag
D-one By Tamdoan Sunscreen 50Diethylamino hydroxybenzoyl hexyl benzoate (2 g/100g) + Adenosine (0.04 g/100g) + Arbutin (2 g/100g) + Octinoxate (7 g/100g) + Octisalate (5 g/100g) + Octocrylene (1 g/100g) + Titanium dioxide (2.54 g/100g) + Zinc oxide (5.99 g/100g)CreamTopicalDran Co.,ltd2019-11-19Not applicableUS flag
Fascy Lab Green Plus SunDiethylamino hydroxybenzoyl hexyl benzoate (1.0 g/50mL) + Bemotrizinol (0.5 g/50mL)CreamTopicalFascy Co,.ltd.2020-04-01Not applicableUS flag
Hydro Multi-shieldDiethylamino hydroxybenzoyl hexyl benzoate (3 g/100mL) + Adenosine (0.04 g/100mL) + Nicotinamide (2 g/100mL) + Octyl triazone (2 g/100mL)CreamTopicalNatuzen Co., Ltd2019-12-06Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
BRING GREEN Tea Tree CICA Cooling SunDiethylamino hydroxybenzoyl hexyl benzoate (3.5 g/100g) + Bemotrizinol (1.5 g/100g) + Octyl triazone (3.0 g/100g) + Polysilicone-15 (2.0 g/100g)StickTopicalCJ Olive Young Corporation2022-08-01Not applicableUS flag
Calming Days Vegan SunscreenDiethylamino hydroxybenzoyl hexyl benzoate (3 g/100mL) + Bisoctrizole (2 g/100mL) + Iscotrizinol (1.2 g/100mL) + Octyl triazone (2.4 g/100mL)GelTopicalMerci Co.2022-10-18Not applicableUS flag
D-one By Tamdoan Bb LightDiethylamino hydroxybenzoyl hexyl benzoate (2 g/100g) + Adenosine (0.04 g/100g) + Arbutin (2 g/100g) + Octinoxate (7 g/100g) + Octisalate (5 g/100g) + Octocrylene (1 g/100g) + Titanium dioxide (2.54 g/100g) + Zinc oxide (5.99 g/100g)CreamTopicalDran Co.,ltd2016-02-232016-09-05US flag
D-one By Tamdoan Bb MediumDiethylamino hydroxybenzoyl hexyl benzoate (2 g/100g) + Adenosine (0.04 g/100g) + Arbutin (2 g/100g) + Octinoxate (7 g/100g) + Octisalate (5 g/100g) + Octocrylene (1 g/100g) + Titanium dioxide (2.54 g/100g) + Zinc oxide (5.99 g/100g)CreamTopicalDran Co.,ltd2019-11-19Not applicableUS flag
D-one By Tamdoan Sunscreen 50Diethylamino hydroxybenzoyl hexyl benzoate (2 g/100g) + Adenosine (0.04 g/100g) + Arbutin (2 g/100g) + Octinoxate (7 g/100g) + Octisalate (5 g/100g) + Octocrylene (1 g/100g) + Titanium dioxide (2.54 g/100g) + Zinc oxide (5.99 g/100g)CreamTopicalDran Co.,ltd2019-11-19Not applicableUS flag
Fascy Lab Green Plus SunDiethylamino hydroxybenzoyl hexyl benzoate (1.0 g/50mL) + Bemotrizinol (0.5 g/50mL)CreamTopicalFascy Co,.ltd.2020-04-01Not applicableUS flag
Hydro Multi-shieldDiethylamino hydroxybenzoyl hexyl benzoate (3 g/100mL) + Adenosine (0.04 g/100mL) + Nicotinamide (2 g/100mL) + Octyl triazone (2 g/100mL)CreamTopicalNatuzen Co., Ltd2019-12-06Not applicableUS flag
PURITO Centella Green Level Safe SunDiethylamino hydroxybenzoyl hexyl benzoate (30 mg/1mL) + Octyl triazone (20 mg/1mL)CreamTopicalHINATURE Inc.2019-07-232019-08-19US flag
SUN PROJECT SILKY CALMING SUN stickDiethylamino hydroxybenzoyl hexyl benzoate (0.49 g/14g) + Bemotrizinol (0.21 g/14g) + Octyl triazone (0.42 g/14g) + Polysilicone-15 (0.28 g/14g)StickTopicalThank You Farmer Co., Ltd.2022-05-31Not applicableUS flag
Sun Project Skin-relief SuncreamDiethylamino hydroxybenzoyl hexyl benzoate (1.5 mg/50mL) + Bisoctrizole (1 mg/50mL) + Iscotrizinol (0.6 mg/50mL) + Octyl triazone (1.2 mg/50mL)CreamTopicalThank You Farmer Co., Ltd.2022-05-30Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzophenones
Direct Parent
Benzophenones
Alternative Parents
Diphenylmethanes / Aryl-phenylketones / Benzoic acid esters / m-Aminophenols / Dialkylarylamines / Benzoyl derivatives / Aniline and substituted anilines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids
show 4 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Amine / Amino acid or derivatives / Aminophenol / Aniline or substituted anilines / Aromatic homomonocyclic compound / Aryl ketone / Aryl-phenylketone / Benzoate ester
show 19 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
ANQ870JD20
CAS number
302776-68-7
InChI Key
FDATWRLUYRHCJE-UHFFFAOYSA-N
InChI
InChI=1S/C24H31NO4/c1-4-7-8-11-16-29-24(28)20-13-10-9-12-19(20)23(27)21-15-14-18(17-22(21)26)25(5-2)6-3/h9-10,12-15,17,26H,4-8,11,16H2,1-3H3
IUPAC Name
hexyl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate
SMILES
CCCCCCOC(=O)C1=CC=CC=C1C(=O)C1=CC=C(C=C1O)N(CC)CC

References

General References
  1. Kawakami CM, Maximo LN, Fontanezi BB, da Silva RS, Gaspar LR: Diethylamino hydroxybenzoyl hexyl benzoate (DHHB) as additive to the UV filter avobenzone in cosmetic sunscreen formulations - Evaluation of the photochemical behavior and photostabilizing effect. Eur J Pharm Sci. 2017 Mar 1;99:299-309. doi: 10.1016/j.ejps.2016.12.031. Epub 2016 Dec 30. [Article]
  2. Gong P, Yuan H, Zhai P, Dong W, Li H: Degradation of organic ultraviolet filter diethylamino hydroxybenzoyl hexyl benzoate in aqueous solution by UV/H2O2. Environ Sci Pollut Res Int. 2015 Jul;22(13):10189-95. doi: 10.1007/s11356-015-4166-7. Epub 2015 Feb 20. [Article]
  3. Couteau C, Chauvet C, Paparis E, Coiffard L: UV filters, ingredients with a recognized anti-inflammatory effect. PLoS One. 2012;7(12):e46187. doi: 10.1371/journal.pone.0046187. Epub 2012 Dec 20. [Article]
  4. European Commission: OPINION ON Diethylamino hydroxybenzoyl hexyl benzoate [File]
ChemSpider
8286957
RxNav
1426392
ChEBI
136006
ZINC
ZINC000034230491
Wikipedia
Diethylamino_hydroxybenzoyl_hexyl_benzoate

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
LotionTopical
GelTopical
StickTopical
CreamTopical
CreamCutaneous; Topical
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)54, Decomposes at 314European Commission SCCP/1166/08
water solubility< 0.01 mg/LEuropean Commission SCCP/1166/08
logP6.2European Commission SCCP/1166/08
Predicted Properties
PropertyValueSource
Water Solubility0.00702 mg/mLALOGPS
logP6.03ALOGPS
logP6.82Chemaxon
logS-4.8ALOGPS
pKa (Strongest Acidic)7.29Chemaxon
pKa (Strongest Basic)3.38Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area66.84 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity117.64 m3·mol-1Chemaxon
Polarizability45.58 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created at December 03, 2015 16:51 / Updated at January 07, 2021 03:13