Menthyl anthranilate
PubChem CID
8633
Structure
Molecular Formula
Synonyms
- MENTHYL ANTHRANILATE
- Meradimate
- 134-09-8
- Meradimate [INN]
- Menthyl-O-aminobenzoate
Molecular Weight
275.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2005-07-29
- Modify:2025-01-11
Description
Meradimate is a monoterpenoid.
Meradimate, before known as menthyl anthranilate, is used in a maximal concentration of 5% in different products as a UV filter. It is currently required to be named as meradimate in all FDA approved OTC products. Meradimate is approved by the FDA and Health Canada to be used as an ingredient in sunblocking products.
MERADIMATE is a small molecule drug with a maximum clinical trial phase of II.
See also: Meptazinol Hydrochloride (annotation moved to).
Chemical Structure Depiction
(5-methyl-2-propan-2-ylcyclohexyl) 2-aminobenzoate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C17H25NO2/c1-11(2)13-9-8-12(3)10-16(13)20-17(19)14-6-4-5-7-15(14)18/h4-7,11-13,16H,8-10,18H2,1-3H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
SOXAGEOHPCXXIO-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
CC1CCC(C(C1)OC(=O)C2=CC=CC=C2N)C(C)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C17H25NO2
Computed by PubChem 2.2 (PubChem release 2021.10.14)
1404094-59-2
menthyl anthranilate
- MENTHYL ANTHRANILATE
- Meradimate
- 134-09-8
- Meradimate [INN]
- Menthyl-O-aminobenzoate
- (5-methyl-2-propan-2-ylcyclohexyl) 2-aminobenzoate
- Anthranilic acid, p-menth-3-yl ester
- Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 2-aminobenzoate
- 2-isopropyl-5-methylcyclohexyl 2-aminobenzoate
- J9QGD60OUZ
- DTXSID3047895
- Cyclohexanol,5-methyl-2-(1-methylethyl)-, 1-(2-aminobenzoate)
- 5-methyl-2-(propan-2-yl)cyclohexyl 2-aminobenzoate
- NCGC00159361-02
- DTXCID3027871
- CAS-134-09-8
- CCRIS 2468
- Menthyl o-aminobenzoate
- EINECS 205-129-8
- UNII-J9QGD60OUZ
- Meradimate [USAN:USP:INN]
- Neo heliopan MA
- Meradimate (USP/INN)
- MERADIMATE [USAN]
- Menthyl anthranilate, 98%
- MERADIMATE [MART.]
- MERADIMATE [USP-RS]
- MERADIMATE [WHO-DD]
- SCHEMBL18884
- 5-Methyl-2-(1-methylethyl)cyclohexanol-2-aminobenzoate
- CHEMBL1597075
- MENTHYL ANTHRANILATE [MI]
- CHEBI:135974
- MERADIMATE [USP MONOGRAPH]
- Tox21_111602
- Tox21_200561
- BBL028008
- STK083062
- AKOS001387784
- AKOS017278349
- DB11096
- Menthyl anthranilate, analytical standard
- NCGC00159361-06
- NCGC00258115-01
- VS-08642
- DB-042217
- NS00008634
- D04927
- 2-aminobenzoic acid (2-isopropyl-5-methyl-cyclohexyl) ester
- Meradimate, United States Pharmacopeia (USP) Reference Standard
- Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 1-(2-aminobenzoate)
- Menthyl anthranilate, Pharmaceutical Secondary Standard; Certified Reference Material
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
275.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
5.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
275.188529040 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
275.188529040 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
52.3 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
20
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
329
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
3
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
177-179 ºC
'MSDS'
63 ºC
'MSDS'
Insoluble
'MSDS'
Semi-standard non-polar
2146.5
Uv absorber
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118
NIST Number
408783
Library
Main library
Total Peaks
72
m/z Top Peak
137
m/z 2nd Highest
119
m/z 3rd Highest
120
Thumbnail
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Parent, Connectivity Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
Meptazinol Hydrochloride (annotation moved to)
Meradimate is used as an active ingredient in sunscreens or as a sunblock factor in different products. It fits under the category of broad-spectrum absorbent agent. These characteristics are important to consider due to the fact that this kind of ingredients can either absorb or reflect UV radiation. It is also important to know the type of rays that cover. UVA rays are the responsible of causing sun damage and reaching deeper layers of the skin while UVB can only cause sunburn in the outer layer of the skin. When an agent is of broad spectrum, this means that this agent is capable of acting in both UVA and UVB rays.
Active ingredient and drug
Meradimate effect provides a low-level, broad-spectrum protecting coverage effect.
Absorption
Meradimate is not absorbed through the skin.
Route of Elimination
As meradimate is not absorbed, this pharmacokinetic property is not relevant.
As meradimate is not absorbed, this pharmacokinetic property is not relevant.
As meradimate is not absorbed, this pharmacokinetic property is not relevant.
Meradimate acts by absorbing both the UVA and UVB radiation, this provides this ingredient with a broad spectrum and it explains why it is highly used in different products such as lip balms, lipsticks, and moisturizers. Its protective effective action does not cover completely the UVA rays as it only reaches 336 nm. This has been proven even thought meradimate has a theoretical protective coverage range between 200-380 nm. Its function is related to the intrinsic structure of meradimate which is an ortho-disubstituted aminobenzoate. This structure allows easy electron delocalization and shifts in the maximum absorption.
EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
Cosmetics -> Uv absorber
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118
As meradimate is not absorbed, this pharmacokinetic property is not relevant.
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=SOXAGEOHPCXXIO-UHFFFAOYSA-N
- CAS Common ChemistryLICENSEThe data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc/4.0/Menthyl anthranilatehttps://commonchemistry.cas.org/detail?cas_rn=134-09-8
- ChemIDplusMeradimate [USAN:USP:INN]https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000134098ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- DrugBankLICENSECreative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)https://www.drugbank.ca/legal/terms_of_useMeradimatehttps://www.drugbank.ca/drugs/DB11096
- EPA DSSToxMenthyl anthranilatehttps://comptox.epa.gov/dashboard/DTXSID3047895CompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- FDA Global Substance Registration System (GSRS)LICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linking
- ChEBI
- Open TargetsLICENSEDatasets generated by the Open Targets Platform are freely available for download.https://platform-docs.opentargets.org/licence
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.html
- Comparative Toxicogenomics Database (CTD)LICENSEIt is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.http://ctdbase.org/about/legal.jspmenthyl anthranilatehttps://ctdbase.org/detail.go?type=chem&acc=C413549
- DailyMed
- EPA Chemical and Products Database (CPDat)Menthyl anthranilatehttps://comptox.epa.gov/dashboard/DTXSID3047895#exposureEPA CPDat Classificationhttps://www.epa.gov/chemical-research/chemical-and-products-database-cpdat
- Japan Chemical Substance Dictionary (Nikkaji)
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.html
- Metabolomics Workbench2-aminobenzoic acid (2-isopropyl-5-methyl-cyclohexyl) esterhttps://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=71492
- National Drug Code (NDC) DirectoryLICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linking
- NCI Thesaurus (NCIt)LICENSEUnless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.https://www.cancer.gov/policies/copyright-reuseNCI Thesaurushttps://ncit.nci.nih.gov
- NIST Mass Spectrometry Data CenterLICENSEData covered by the Standard Reference Data Act of 1968 as amended.https://www.nist.gov/srd/public-lawCyclohexanol, 5-methyl-2-(1-methylethyl)-, 2-aminobenzoatehttp://www.nist.gov/srd/nist1a.cfm
- NORMAN Suspect List ExchangeLICENSEData: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0https://creativecommons.org/licenses/by/4.0/NORMAN Suspect List Exchange Classificationhttps://www.norman-network.com/nds/SLE/
- SpectraBaseNEO HELIOPAN, TYPE MAhttps://spectrabase.com/spectrum/ECGC4dVBmmSMenthyl anthranilatehttps://spectrabase.com/spectrum/IcvSYVoq7FDMenthyl anthranilatehttps://spectrabase.com/spectrum/3U5H2pKdodYMenthyl anthranilatehttps://spectrabase.com/spectrum/VDjj9aO3Fh
- Springer Nature
- Wikidata(5-methyl-2-propan-2-ylcyclohexyl) 2-aminobenzoatehttps://www.wikidata.org/wiki/Q100553704
- WikipediaMenthyl anthranilatehttps://en.wikipedia.org/wiki/Menthyl_anthranilate
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmlmenthyl anthranilatehttps://www.ncbi.nlm.nih.gov/mesh/67413549
- GHS Classification (UNECE)GHS Classification Treehttp://www.unece.org/trans/danger/publi/ghs/ghs_welcome_e.html
- Consumer Product Information Database (CPID)LICENSECopyright (c) 2024 DeLima Associates. All rights reserved. Unless otherwise indicated, all materials from CPID are copyrighted by DeLima Associates. No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.https://www.whatsinproducts.com/contents/view/1/6Consumer Products Category Classificationhttps://www.whatsinproducts.com/
- EPA Substance Registry ServicesEPA SRS List Classificationhttps://sor.epa.gov/sor_internet/registry/substreg/LandingPage.do
- EPA Chemicals under the TSCAEPA TSCA Classificationhttps://www.epa.gov/tsca-inventory
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 403381452https://pubchem.ncbi.nlm.nih.gov/substance/403381452
- NCBI
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