
L’acide déhydroacétique ou déshydroacétique est un composé organique dérivé d’une pyrone, utilisé comme fongicide, bactéricide et régulateur de pH. Il est utilisé comme additif alimentaire sous le numéro E265. Fongicide, utilisé pour conserver les cornichons et les fraises. D’origine synthétique vraisemblablement fabriqué à partir de cétène. Aux États-Unis, son utilisation est limitée au traitement des légumes de la famille des courges, comme conservateur, dans la limite de 65 ppm résiduels dans le légume préparé. Il permet aussi bien d’éviter le pourrissement des fruits lors de leur stockage, que de préserver la propreté microbiologique des cosmétiques au moment de leur emploi.
Autres noms
Francais | Anglais |
Acide déhydracétique | Dehydroacetic acid |
3-Acetyl-6-methyl-2H-pyran-2,4(3H)-dione | dehydroacetic acid ion (1-) |
3-ACETYL-4-HYDROXY-6-METHYL-2H-PYRAN-2-ONE | dehydroacetic acid, potassium ion (1-) |
3-ACETYL-6-METHYL-2,4-PYRANDIONE | dehydroacetic acid, sodium ion (1-) |
3-ACETYL-6-METHYLDIHYDROPYRANDIONE-2,4 | dehydroacetic acid, sodium monohydrate ion (1-) |
3-ACETYL-6-METHYLPYRANDIONE-2,4 | dehydroacetic acid, zinc ion (1-) |
4-HEXENOIC ACID, 2-ACETYL-5-HYDROXY-3-OXO-, DELTA-LACTONEACETYL-3 METHYL-6 PYRANDIONE-2,4 | DHA-S |
Acide déhydroacétique | DHAS |
METHYLACETOPYRONONE | dihydroxyacetone sulfate |
Autres langues ; Acido deidroacetico, Dehydroessigsäure, Ácido deshidroacético
Fonction et caractéristiques
Conservateur fongicide
CARACTÉRISTIQUES
Poudre de couleur jaune pâle, à propriétés antibactériennes et antifongiques. Peu soluble dans l’eau.
Utilisations
Conservateur alimentaire et dans les cosmétiques en tant que conservateur antimicrobien
Utilisations détaillées
# | Category | Category Description |
1 | Chemical, laboratory | Modifier used for chemical, when chemical is used in a laboratory |
2 | Consumer_use | Term applied when the only information the source indicates is ‘consumer’ or ‘consumer product’ ; also applied to terms that the source indicates are f |
3 | Decor, candle, detected | Chemicals detected in substances or products (note that these chemicals may be absent from an ‘ingredient list’ for the product and thus unexpected, but have been detected in product testing studies) |
4 | Drug | Drug product, or related to the manufacturing of drugs; modified by veterinary, animal, or pet if indicated by source |
5 | Drug, inactive_ingredient | Pharmaceutical related |
6 | Food | Food for human consumption, does not include food additives (see food_additive); also includes manufacture of food, facilities related to food (with appropriate modifiers) |
7 | Food_additive | Includes spices, extracts, colorings, flavors, etc added to food for human consumption |
8 | Food_contact | Includes food packaging, paper plates, cutlery, small appliances such as roasters, etc.; does not include facilities that manufacture food |
9 | Fragrance | Fragrances or odor agents, can be used in home products (cleaners, laundry products, air fresheners) or similar industrial products; usage indicated when known; more specific modifiers included when known |
10 | Industrial_manufacturing | |
11 | Inert | |
12 | Manufacturing, chemical | General term used only when the only information known from the source is ‘chemical,’ typically related to manufacturing of chemicals, or laboratory chemicals |
13 | Manufacturing, personal_care | Personal care products, including cosmetics, shampoos, perfumes, soaps, lotions, toothpastes, etc |
14 | Manufacturing, personal_care, cosmetics, perfume | Fragrance used as a personal care product |
15 | Personal care: hair conditioner | Rinse-out everyday hair conditioners (excluding combo shampoo/conditioner products) |
16 | Personal_care | Personal care products, including cosmetics, shampoos, perfumes, soaps, lotions, toothpastes, etc |
17 | Personal_care, cosmetics | Subcategory of personal_care, includes fragrances, shampoos, make-up, etc.; appropriate modifiers included when known |
18 | Personal_care, cosmetics, eye | General term for personal care products related to the eye (e.g. eye care products) |
19 | Personal_care, cosmetics, face | Personal care products used on the face (includes facial treatments, oil and blemish control, make-up removers, facial cleansers) |
20 | Personal_care, cosmetics, hair | General products related to the hair (hair tools, hair salons, shampoo, conditioner, hair dye); more specific modifiers included when known |
21 | Personal_care, cosmetics, lotion, detected | Chemicals detected in substances or products (note that these chemicals may be absent from an ‘ingredient list’ for the product and thus unexpected, but have been detected in product testing studies) |
22 | Personal_care, cosmetics, perfume | Fragrance used as a personal care product |
23 | Personal_care, cosmetics, preservatives | Includes preservatives used in cosmetics, film, wood preserving agents, foods, etc (note food preservatives are also indicated as food_additive) |
24 | Personal_care, cosmetics, skin | Personal care products indicated for use on the skin (note applied when source indicates ‘skin’) |
25 | Personal_care, cosmetics, soap, detected | Chemicals detected in substances or products (note that these chemicals may be absent from an ‘ingredient list’ for the product and thus unexpected, but have been detected in product testing studies) |
26 | Personal_care, sexual_wellness, gel, detected | Chemicals detected in substances or products (note that these chemicals may be absent from an ‘ingredient list’ for the product and thus unexpected, but have been detected in product testing studies) |
27 | Personal_care, sunscreen, detected | Chemicals detected in substances or products (note that these chemicals may be absent from an ‘ingredient list’ for the product and thus unexpected, but have been detected in product testing studies) |
28 | Personal_care, wash, body | Personal care products for general use on the body (body makeup, body powder, body treatments, body cleansers) |
29 | Pesticide | Substances used for preventing, destroying or mitigating pests |
30 | Pesticide, biocide, active_ingredient | Active ingredients in a product (often active ingredients in pesticide, if so also tagged with ‘pesticide’) |
31 | Pesticide, inert_ingredient | Inert ingredients in a pesticide |
32 | Pesticide, preservatives | Includes preservatives used in cosmetics, film, wood preserving agents, foods, etc (note food preservatives are also indicated as food_additive) |
33 | Preservatives | Includes preservatives used in cosmetics, film, wood preserving agents, foods, etc (note food preservatives are also indicated as food_additive) |
34 | Softener | Softeners for plastic, rubber, paint, or adhesives, or generic ‘softeners’ |
35 | Stabilizer | General stabilizers, application unknown |
36 | Water_treatment | Includes water softeners, lime removers, and the products used in the process of the collection, purification, and distribution of water |
Toxicité
TOXIQUE
Les risques
Il n’a pas de toxicité démontrée même à long terme, à des doses de 10 mg/kg de poids corporel pendant 150 jours, mais à très hautes doses, il est source de nausées, ataxie, voire convulsions, et a hautes doses entrave la fonction rénale et/ou cause des insuffisances rénales.
Effets secondaires Actuellement (2018) très peu de données toxicologiques disponibles concernant la substance dans l’alimentation transformée. La substance pure (vrac) est notamment classée Xn (Nocif) et R22 (Nocif par ingestion). La DL50 (Dose Létale min. pour tuer 50% des animaux de laboratoire, ici des rats/voie orale) rapportée est de 500 mg/kg. Un extrait de la National Library of Medicine (NLM) américaine, et de la Fiche de Données de Sécurité (FDS) du fournisseur ScienceLab rapportent de la nocivité pour les reins, voire aussi (FDS) le foie, le SNC, et d’autres organes cibles par utilisations répétées/prolongées.
Le Registry of Toxic Effects of Chemical Substances (RTECS, USA) rapporte – entre autres – des tumeurs chez les rats de laboratoire, par voie subcutanée. Une cancérogénicité pour l’homme, basée sur des résultats avec l’animal, n’est pas exclue, rapporte ScienceLab . Chez l’animal, le produit traverse le placenta. Il est trouvé dans le lait maternel.
RÉSIDUS AUTORISÉS (dits Critères de pureté)
Information non disponible.
Dosage maximum dans les produits transformés
Aux États- Unis limite de 65 ppm résiduels dans le légume préparé
Canada
Liste des agents de conservation autorisés (Listes des additifs alimentaires autorisés)
Non listé
Liste des additifs alimentaires autorisés ayant d’autres utilisations acceptées
Non listé
DSL – Liste intérieure des substances
Non listé
Liste des Produits chimiques préoccupants, non règlementé
Non listé
États-Unis
Liste des substances ajoutées aux aliments Substances Added to Food (formerly EAFUS)
Substance | DEHYDROACETIC ACID | |
Used for (Technical Effect) | ANTIMICROBIAL AGENT | |
Document Number (21 CFR) | 172.130 175.105 | |
TITLE 21–FOOD AND DRUGS | ||
CHAPTER I–FOOD AND DRUG ADMINISTRATION DEPARTMENT OF HEALTH AND HUMAN SERVICES | ||
SUBCHAPTER B – FOOD FOR HUMAN CONSUMPTION (CONTINUED) | ||
PART 172 — FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION
Subpart B – Food Preservatives
Sec. 172.130 Dehydroacetic acid. |
The food additive dehydroacetic acid and/or its sodium salt may be safely used in accordance with the following prescribed conditions: (a) The food additive meets the following specifications: Dehydroacetic acid: Melting point, 109 deg.C-111 deg.C; assay, minimum 98 percent (dry basis). Sodium salt of dehydroacetic acid: Assay, minimum 98 percent (dry basis). (b) It is used or intended for use as a preservative for cut or peeled squash, and is so used that no more than 65 parts per million expressed as dehydroacetic acid remains in or on the prepared squash. (c) The label or labeling of any package of the additive intended for use in food shall bear adequate directions for use to insure compliance with this section. |
TITLE 21–FOOD AND DRUGS |
CHAPTER I–FOOD AND DRUG ADMINISTRATION DEPARTMENT OF HEALTH AND HUMAN SERVICES |
SUBCHAPTER B – FOOD FOR HUMAN CONSUMPTION (CONTINUED) |
PART 175 — INDIRECT FOOD ADDITIVES: ADHESIVES AND COMPONENTS OF COATINGS
Subpart B – Substances for Use Only as Components of Adhesives
Sec. 175.105 Adhesives. |
(a) Adhesives may be safely used as components of articles intended for use in packaging, transporting, or holding food in accordance with the following prescribed conditions: (1) The adhesive is prepared from one or more of the optional substances named in paragraph (c) of this section, subject to any prescribed limitations. (2) The adhesive is either separated from the food by a functional barrier or used subject to the following additional limitations: (i) In dry foods. The quantity of adhesive that contacts packaged dry food shall not exceed the limits of good manufacturing practice. (ii) In fatty and aqueous foods. (a ) The quantity of adhesive that contacts packaged fatty and aqueous foods shall not exceed the trace amount at seams and at the edge exposure between packaging laminates that may occur within the limits of good manufacturing practice. (b ) Under normal conditions of use the packaging seams or laminates will remain firmly bonded without visible separation. (b) To assure safe usage of adhesives, the label of the finished adhesive container shall bear the statement “food-packaging adhesive”. (c) Subject to any limitation prescribed in this section and in any other regulation promulgated under section 409 of the Act which prescribes safe conditions of use for substances that may be employed as constituents of adhesives, the optional substances used in the formulation of adhesives may include the following: (1) Substances generally recognized as safe for use in food or food packaging. (2) Substances permitted for use in adhesives by prior sanction or approval and employed under the specific conditions of use prescribed by such sanction or approval. (3) Flavoring substances permitted for use in food by regulations in this part, provided that such flavoring substances are volatilized from the adhesives during the packaging fabrication process. (4) Color additives approved for use in food. (5) Substances permitted for use in adhesives by other regulations in this subchapter and substances named in this subparagraph: Provided, however, That any substance named in this paragraph and covered by a specific regulation in this subchapter, must meet any specifications in such regulation. Substances Limitations Dehydroacetic acid |
UNII Code | Active Ingredient | Monograph |
2KAG279R6R | Répertorié comme une substance d’ingrédient |
Listé
EUROPE
Listé EINECS(European INventory of Existing Commercial chemical Substances)
Name | EC no. | CAS no. | Description | Molecular Formula | |
3-acetyl-6-methyl-2H-pyran-2,4(3H)-dione IUPAC name: Dehydroacetic Acid | 208-293-9 | 520-45-6 | C8H8O4 | Details | |
Sodium 1-(3,4-dihydro-6-methyl-2,4-dioxo-2H-pyran-3-ylidene)ethanolate Public name: Sodium dehydracetate, Dehydroacetic acid sodium salt, 3-(1-Hydroxyethylidene)-6-methyl-2H-pyran-2,4(3H)-dione sodium salt | 224-580-1 | 4418-26-2 | C8H7O4.Na |
Flavor and Extract Manufacturers Association (FEMA)
Avantages
Empêche la croissance des microbes.
Source de l’additif
Origine
Synthétique
Végétale | Non | Animale | Non | Minérale | Non | Synthétique | Oui |
Convient aux régimes
Végétarien | Oui | Végétalien | Oui | Hallal | Oui | Kosher | Oui |
Biologique | Non | Sans gluten | Oui | Sans noix | Oui | Sans œufs | Oui |
Compatible Bio (Référentiel COSMOS)
Autorisé dans les pays suivants
Country | Status | Matched Term |
États-Unis | Approved | Dehydroacetic acid or its Na salt |
Utilisation restreinte
Pays non identifié
Utilisation interdite
Country | Status | Matched Term |
European Union | Not Permitted | |
Australia and New Zealand | Not Permitted |
Philippines | Not Permitted | |
Autriche | Not Permitted | |
Belgique | Not Permitted | |
Bulgarie | Not Permitted | |
Chypre | Not Permitted | |
République tchèque | Not Permitted | |
Danemark | Not Permitted | |
Estonie | Not Permitted | |
Finlande | Not Permitted | |
France | Not Permitted | |
Allemagne | Not Permitted | |
Grèce | Not Permitted | |
Hongrie | Not Permitted | |
Irlande | Not Permitted | |
Italie | Not Permitted | |
Lettonie | Not Permitted | |
Lituanie | Not Permitted | |
Luxembourg | Not Permitted | |
Malte | Not Permitted | |
Pays-Bas | Not Permitted | |
Pologne | Not Permitted | |
Portugal | Not Permitted | |
Roumanie | Not Permitted | |
Slovaquie | Not Permitted | |
Slovénie | Not Permitted | |
Espagne | Not Permitted | |
Suède | Not Permitted | |
Royaume-Uni | Not Permitted | |
Australie | Not Permitted | |
Nouvelle-Zélande | Not Permitted |
Spécification technique
- CAS : 520-45-6 / 771-03-9 / 16807-48-0 –
- Formule moléculaire; C8H8O4
- EINECS Number: 208-293-9 / 212-227-4 / –
Additifs similaires
Conservateurs | Conservateurs | Conservateurs | Conservateurs |
E202 | E220 | E250 | E211 |
Sorbate de potassium | Dioxyde de soufre | Nitrite de sodium | Benzoate de sodium |
Ou peut-on retrouvé
Cosmétique, additif alimentaire, emballage, composantes des saveurs, produit pharmaceutique.
Exemple de catégories de produits alimentaires transformés contenant l’additif
- Fromages
- Croute des fromages
- Cornichons
- Fraises
- Courges
- Il est utilisé ou destiné à être utilisé comme agent de conservation pour les courges coupées ou pelées
Autres applications non alimentaires
Cosmétiques et soins de la peau
L’acide déhydroacétique est utilisé dans les cosmétiques en tant que conservateur pour ses actions de fongicide et bactéricide. Comme il est Biodégradable, ce produit chimique ne pose pas de problème pour l’environnement, et les risques pour la santé restent assez faible. Notez toutefois, que le composé est interdit dans les sprays de type aérosol. L’acide déhydroacétique est autorisé en cosmétique Bio.
Restriction en Europe : La concentration maximale autorisée dans les préparations cosmétiques prêtes à l’emploi est de 0,6 % (en acide). Il est interdit de l’utiliser dans les sprays de type aérosol
Ses fonctions (INCI)
Conservateur : Inhibe le développement des micro-organismes dans les produits cosmétiques.
- Cet ingrédient est présent dans 5.83% des cosmétiques.
- Lingettes démaquillantes (27,56%)
- Lingettes nettoyantes visage (24,86%)
- Lingettes nettoyantes bébé (19,17%)
- Crème visage nuit (16,04%)
- Soin contour des yeux (14,69%)
Example de produit cosmétique en contenant:
Et
Et
Liste EWG
foundation | 121 products |
conditioner | 110 products |
shampoo | 76 products |
eye shadow | 65 products |
facial moisturizer/treatment | 53 products |
facial cleanser | 51 products |
body wash/cleanser | 46 products |
hair treatment/serum | 40 products |
moisturizer | 37 products |
serums & essences | 36 products |
makeup remover | 34 products |
facial powder | 28 products |
blush | 27 products |
mask | 24 products |
liquid hand soap | 22 products |
hair styling aide | 21 products |
bronzer/highlighter | 21 products |
exfoliant/scrub | 21 products |
hand cream | 17 products |
lip balm | 17 products |
body firming lotion | 16 products |
styling gel/lotion | 13 products |
mascara | 11 products |
toners/astringents | 10 products |
lipstick | 10 products |
makeup primer | 9 products |
moisturizer with SPF | 8 products |
around-eye cream | 8 products |
baby wipes | 7 products |
detangler | 6 products |
baby shampoo | 6 products |
hair spray | 6 products |
eye makeup remover | 6 products |
eye liner | 5 products |
setting powder/spray | 5 products |
baby soap | 4 products |
beach & sport sunscreen | 4 products |
beard cleanser | 4 products |
fragrance for women | 4 products |
beard care | 4 products |
BB cream | 4 products |
foot moisturizer | 4 products |
bath oil/salts/soak | 3 products |
bubble bath | 3 products |
brow liner | 3 products |
hair color and bleaching | 3 products |
concealer | 3 products |
shaving cream | 3 products |
after sun product | 2 products |
after shave | 2 products |
sunless tanning | 2 products |
baby bubble bath | 1 products |
lip balm with SPF | 1 products |
lip gloss | 1 products |
cuticle treatment | 1 products |
bar soap | 1 products |
nail treatment | 1 products |
hair-loss treatment | 1 products |
oil controller | 1 products |
beard oil | 1 products |
Pharmaceutique
L’ACIDE DÉSHYDROACETIQUE est couramment inclus dans les médicaments sous les formes suivantes.
Route | Forme posologique | Puissance |
LOTION | TOPIQUE | 0,1% P/ P |
SHAMPOOING | TOPIQUE | NA |
Autres informations
L’acide déhydroacétique (E)265 et le déhydroacétate de sodium (E)266 étaient listés en 2015 comme conservateurs au Codex alimentarius, mais ils sont aujourd’hui délistés (selon liste SIN 2017). L’acide déhydroacétique et/ou son sel le déhydroacétate de sodium, sont également utilisés dans les produits de la parapharmacie, dans des dentifrices dits anti-enzymes, comme conservateurs dans les cosmétiques, comme plastifiants pour résine synthétique.
Des propriétés antimicrobiennes avant tout
Les propriétés antimicrobiennes de l’acide déhydroacétique ont été découvertes après le Seconde Guerre mondiale. Utilisé sous forme acide ou sous forme de son sel de sodium, indifféremment, ce conservateur exerce un effet antifongique par altération de la membrane cellulaire des microorganismes. A faible concentration, le déhydroacétate de sodium a une activité bactériostatique qui s’exerce vis-à-vis de nombreux germes; cet effet peut être renforcé par synergie avec la monolaurine ou des acides organiques. Comparé au sorbate de potassium, le déhydroacétate de sodium possède une activité bactériostatique plus forte et ce quel que soit le pH du milieu considéré.
Une incompatibilité avec les générateurs de formol
Dans les années 1980–1990, on associe fréquemment le déhydroacétate de sodium à des générateurs de formol (imidazolidinylurée, bromo-nitropropanediol…) dans les cosmétiques, afin d’assurer leur conservation. On se rend alors compte qu’il y a formation d’un précipité. Ceci entraîne une baisse d’efficacité du conservateur car la molécule générée ne possède pas d’activité antimicrobienne. Ce problème a longtemps gêné les chercheurs qui ont cherché pendant de nombreuses années à mettre au point des systèmes ingénieux (mise au point d’emballage renfermant du déhydroacétate de sodium susceptible d’être libéré au moment de l’ouverture du cosmétique) afin d’éviter la perte d’efficacité du système conservateur au fil du temps. Le plus sage reste sûrement de ne plus avoir recours aux générateurs de formol, tout simplement !
Quelques cas d’allergie déclarés
L’acide déhydroacétique est un conservateur sûr d’emploi. Quelques cas d’allergies ont cependant été déclarés chez des personnes souffrant d’ulcères de la jambe traités à l’aide de spécialités cicatrisantes, antifongiques ou anti-prurigineuses.
Un conservateur qui franchit les portes de l’hôpital
La sécheresse cutanée extrême touche un grand nombre de sujets âgés. Ce phénomène peut être aggravé par une toilette réalisée avec des produits asséchants. Afin d’éviter d’aggraver cette xérose au moment des soins d’hygiène, des équipes belges ont proposé l’utilisation, lors du nursing, de gants imbibés d’un produit nettoyant (Aqua, Propylene Glycol, Coco-Glucoside, Phenoxyethanol, Parfum, Benzoic acid, Polyaminopropyl Biguanide, Octyldodecanol, Aloe Barbadensis Extract, Glycine Soja Oil, Dehydroacetic Acid, Sodium Lauroamphoacetate, Calendula Officinalis Extract, Tilia Cordata Extract, Melissa Officinalis Extract, Hamamelis Virginiana Extract, Echinacea Purpurea Extract, Chamomilla Recutita Extract, Centella Asiatica Extract, Aloe Barbadensis Gel, Tocopherol).
La fréquence de survenue d’eczéma au niveau des mains est élevée parmi le personnel soignant ; afin de limiter ce phénomène lié à l’utilisation fréquente de solutions désinfectantes, il est possible d’utiliser une crème barrière protectrice. Celle proposée par des équipes allemandes en 2017 est conservée, entre autres, à l’aide d’acide déhydroaétique. La formule de l’émulsion est la suivante: octyloctanoate, polyglyceryl-2-dipolyhydroxystearate, dioctylcyclohexane, glycerol, Buxus chinensis (jojoba oil), Cera alba (beeswax), panthenol, magnesium sulfate, hydrolyzed wheat protein, allantoin, methylparaben, propylparaben, phenoxyethanol, dehydroacetic acid, sorbic acid, benzoic acid, lactic acid. Pour notre part, il ne nous parait pas judicieux d’incorporer dans ce type de formule un hydrolysat de protéines de blé, celui-ci étant connu pour être susceptible d’engendrer diverses manifestations allergiques chez les coiffeurs mis au contact avec des cosmétiques en contenant.14
L’acide déhydroacétique, en bref
Incompatibles avec les générateurs de formol (c’est une bonne nouvelle pour nous qui sommes incompatibles avec cette catégorie de conservateurs), adaptables et tout terrain, l’acide déhydroacétique et son sel de sodium sont des conservateurs antimicrobiens sûrs qui n’ont pas besoin de longs argumentaires publicitaires pour être choisis par les formulateurs.
Bibliographie
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- 2H-Pyran-2,4(3H)-dione, 3-acetyl-6-methyl-, https://spectrabase.com/spectrum/GHMKffQNnSl
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- 2H-Pyran-2,4(3H)-dione, 3-acetyl-6-methyl-, https://spectrabase.com/spectrum/Eevca4aKIwC
- 2H-Pyran-2,4(3H)-dione, 3-acetyl-6-methyl-, https://spectrabase.com/spectrum/CwCrzc0wJRw
- 2H-Pyran-2,4(3H)-dione, 3-acetyl-6-methyl-,https://spectrabase.com/spectrum/7S1gWNNcYQi
- 2H-Pyran-2,4(3H)-dione, 3-acetyl-6-methyl-,https://spectrabase.com/spectrum/7rJeuvjWZqi
- 2H-Pyran-2,4(3H)-dione, 3-acetyl-6-methyl-,https://spectrabase.com/spectrum/1isOAkbsKzA
- 2H-Pyran-2,4(3H)-dione, 3-acetyl-6-methyl-,https://spectrabase.com/spectrum/DGYGF446RWa
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