Methyl N-methylanthranilate is a methyl ester resulting from the formal condensation of the carboxy group of N-methylanthranilic acid with methanol.
Definition
Methyl N-methylanthranilate is a methyl ester resulting from the formal condensation of the carboxy group of N-methylanthranilic acid with methanol. It has a role as an animal metabolite, a plant metabolite and a fungal metabolite. It is a methyl ester, a benzoate ester, a substituted aniline and a secondary amino compound. It is functionally related to a N-methylanthranilic acid.
Source: PubChem
US FDA substance register · UNII 5Z37T562P9 · registered name DIMETHYL ANTHRANILATE · single chemical substance
Methyl-N-methylanthranilate is a fragrance ingredient used in various cosmetics, including fine fragrances, shampoos, soaps and other toiletries as well as in non-cosmetic products such as household cleaners and detergents.
Cosmetic roles
Safety & regulatory references
- Restricted
- European Union · International fragrance standard (IFRA) · United Kingdom
Source: ASEAN Cosmetic Directive · EU Cosmetics Regulation · Health Canada Cosmetic Ingredient Hotlist · IFRA fragrance standards · MFDS (Korea) cosmetic regulatory information · UK cosmetics regulations (OPSS)
ASEAN
- Field of application and/or use : (a) Leave-on products (b) Rinse-off products
- Maximum authorised concentration in the finished cosmetic product : (a) 0,1 % (b) 0,2 %
- Other limitations and requirements : For (a): Not to be used in sunscreen products and products marketed for exposure to natural or artificial UV light. For (a) and (b): — Do not use with nitrosating agents — Maximum nitrosamine content: 50 μg/kg — Keep in nitrite-free containers
Canada
- Maximum Concentration Permitted : 0.1%
유럽
- Product Type, body parts : (a) Leave-on products (b) Rinse-off products
- Maximum concentration in ready for use preparation : (a) 0,1 % (b) 0,2 %
- Other : For (a): Not to be used in sunscreen products and products marketed for exposure to natural or artificial UV light. For (a) and (b): — Do not use with nitrosating agents — Maximum nitrosamine content: 50 μg/kg — Keep in nitrite-free containers
Source: MFDS (Korea) cosmetic regulatory information
Not classified under Korea’s toxic-substance GHS list · existing chemical substance
EU Cosmetics Regulation, Annex III (restricted substances), entry 323 · maximum concentration (a) 0,1 % (b) 0,2 % · applies to (a) Leave-on products (b) Rinse-off products
Restriction Annex III/323 · SCCS opinion: Methyl-N-methylanthranilate Phototoxicity only; Opinion on Methyl-N-methylanthranilate (photo-toxicity only); Scientific Advice on the SCCS Opinion on methyl-N-methylanthranilate (MNM)(SCCS/1455/11).
Source: EU CosIng ingredient list
More data — names, identifiers, properties, test records, literature
Names & identifiers
- CAS No.chemical registry number
- 85-91-6
- EC No.EU chemical inventory number
- 201-642-6
- DTXSIDUS EPA chemical ID
- DTXSID1052581
- DTXCIDUS EPA compound ID
- DTXCID8031154
- IUPAC
- Methyl 2-(methylamino)benzoate
- Molecular formula
- C9H11NO2
- Molecular weight
- 165.192 g/mol
Measured properties
- Appearance
- Colorless or pale yellow liquid with an odor of grapes, [Hawley] Pale-yellow liquid with a slightly blue fluorescence or solid, Odor like orange peels, mp = 18.5-19.5 deg C, [HSDB] · Liquid
- Odour
- ORANGE & MANDARIN-PEEL-LIKE ODOR
- Boiling point
- 256 °C @ 760 MM HG · 255.00 to 256.00 °C. @ 760.00 mm Hg
- Melting point
- 18.5-19.5 °C · 19 °C
- Solubility
- INSOL IN WATER, SOL IN ALCOHOL, ETHER · SOL IN MOST COMMON ORGANIC SOLVENTS
- Density
- 1.120 @ 15 °C · 1.124-1.132
- Melting/freezing point
- 17 ℃(18.5~19.5℃(HSDB))
- Initial boiling point and range
- 258 ℃(256℃(HSDB))
- Relative density
- 1.120 (15℃)
- Molecular weight
- 165.19
Values measured on the substance itself. The KOSHA data are a reference for writing and reviewing safety data sheets, not a specification for a commercial raw material.
Source: PubChem · KOSHA safety data sheets (Korea)
What products actually use it for
What the 59 products reported to the US EPA with this ingredient use it for. Products outside cosmetics are included, so the top few rows are its main uses.
- Fragrance56
- Flavouring and nutrient3
Source: US EPA CompTox dashboard
Irritation and sensitisation studies
4 skin studies and 2 eye studies are on record.
The study conclusions largely agree (100%). These tests are on the raw material itself; irritation at the amount in a finished product is a different question.
See all 6 studies
- Studies Indicate No Significant Irritation
skin irritation: in vivo · Screening · other guideline: as mentioned below according to - Not likely to be sensitizing
skin sensitisation: in vivo (non-LLNA) · Screening · according to other guideline: as mentioned below - Category 6.3A (Category 2)
Skin Irritation · Read Across - Not likely to be sensitizing
skin sensitisation · Screening · according to other guideline: as mentioned below - Category 6.4A (Category 2A)
Eye Irritation · Read Across - Severe Irritation
eye irritation: in vivo · Screening · other guideline: as mentioned below equivalent or similar to
Source: US EPA CompTox dashboard
Related literature
- UVR-induced phototoxicity mechanism of methyl N-methylanthranilate in human keratinocyte cell line. · 2022
- Phototoxic risk assessment of dermally-applied chemicals with structural variety based on photoreactivity and skin deposition. · 2020
- Scientific Opinion on the safety and efficacy of anthranilate derivatives (chemical group 27) when used as flavourings for all animal species. · 2011
- Hepatic Metabolism of Methyl Anthranilate and Methyl N-Methylanthranilate as Food Flavoring Agents in Relation to Allergenicity in the Guinea Pig · 2005
Linked databases 22
- ASEAN Cosmetic Directive
- Australian Industrial Chemicals Inventory (AICIS)
- ChEBI
- ChEMBL
- EU CosIng ingredient list 2
- EU Cosmetics Regulation
- EU restricted substances (Annex III)
- Health Canada Cosmetic Ingredient Hotlist
- IFRA fragrance standards
- Korea toxic substances GHS register (NIER)
- KOSHA safety data sheets (Korea)
- MFDS (Korea) cosmetic regulatory information 2 3
- NIST Chemistry WebBook
- PubChem 2
- Tlooto literature search 2 3 4
- UK cosmetics regulations (OPSS)
- UniChem cross-reference IDs
- US EPA CompTox dashboard 2
- US EPA DSSTox chemical database
- US FDA substance registration (GSRS)
- US FDA Unique Ingredient Identifier (UNII)
- Wikidata