Retinol, acetate
Basic information
- CAS
127-47-9- Standard SMILES
CC(=O)OC/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C- InChIKey
QGNJRVVDBSJHIZ-QHLGVNSISA-N- Molecular formula
- C22H32O2
- Average molar mass
- 328.5 g/mol
- Monoisotopic mass
- 328.24023026
Overview
Retinyl acetate is an acetate ester. It is functionally related to an all-trans-retinol.
Names & identifiers
- Preferred name
- Retinol, acetate
- IUPAC
- [(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] acetate
- English name
- Retinyl acetate
- Molecular formula
- C22H32O2
- Molecular weight
- 328.49
Names & synonyms
RETINYL ACETATEVitamin A acetateRetinol acetate127-47-9Retinol, acetateVitamin A1 acetateall-trans-Retinol acetateCrystaletsVitamin A alcohol acetateDavitan A 650all-trans-Vitamin A acetateRetinol, acetate, all-trans-
Show more names
retinylVITAMIN A ACETATALL-TRANS-RETINYL ACETATERetinylacetatRETINOL ACETATE ALL TRANSMyvakMyvax
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl acetateall-trans-RetinylacetateAcetic acid, retinyl ester[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] acetateDTXSID60212403LE3D9D6OYVitamin A, acetateVitamin A acetate (tritiated)
Database identifiers
- CAS
127-47-9、64536-04-5- PubChem CID
- 638034
- DTXSID
DTXSID6021240- ChEMBL
CHEMBL486193
Properties
Computed structural properties
- XLogP
- 6.3
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 7
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 595
Experimental & physicochemical properties
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> Retinoids [PR0109]
CosmeticsSkin conditioning
SpringerMaterials PropertiesChemical diffusion
Food AdditivesNUTRIENT SUPPLEMENT -> FDA Substance added to food
Physicochemical properties
- Melting point
- 57 · 57-58 °C
- Boiling point
- 406.22 °C · 406.22°C (rough estimate)
- Density
- 1.0474 · 1.0474 (rough estimate)
- refractive index
- 1.547 · 1.547-1.555
- Flash point
- 14 ℃ · 14℃
- storage temp.
- 2 · 2-8°C
- solubility
- 25 mg/mL · absolute ethanol: 25 mg/mL
- form
- solid or viscous liquid
- color
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 0.3% (1 of 374) of reports.
Danger
H315 (83.4%): Causes skin irritation [Warning Skin corrosion/irritation]
P203, P264, P273, P280, P302+P352, P318, P321, P332+P317, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 374 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Retinol, acetate
Regulation (EC) No 1831/2003 (amended)
REACH registered substance: Retinyl acetate (EC: 204-844-2)
Retinol acetate: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (83.4%)
Toxicology
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- F
- 1-8-10
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- VH6825000
- ridadr
- UN1170 - class 3 - PG 2 - Ethanol
- hs_code
- 29362100
- Toxicity
- LD50 (10 day) orally in mice: 4100 mg/kg (Kamm)
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity.
Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved.
Uses & manufacturing
Household ProductsInformation on 4 consumer products that contain Retinyl acetate in the following categories is provided:
Use ClassificationCosmetics -> Skin conditioning
General Manufacturing InformationRetinol, acetate: ACTIVE
Applications
DescriptionRetinyl acetate (retinol acetate, vitamin A acetate,127-47-9) is a natural form of vitamin A. It is the acetate ester of retinol. It consists of yellow crystals which are greasy or sticky. It has a mild, characteristic odor. It has potential antineoplastic and chemo-preventive activities. It can be used to fortify food with vitamin A. As vitamin A acetate can induce cell differentiation and inhibit cell proliferation, it is used in skin-conditioning agent.
UsesEssential micronutrient
Usesvitamin precursor
Retinyl acetate has been used: a control diet to study its effect at different developmental periods in fish larvae to study its inhibitory effects on Mycobacterium aviumsubspeciesparatuberculosis(MAP) strains as an internal standard in high performance liquid chromatography (HPLC) to quantify vitamin A in fortified milk
Related reactions
6 records
Compound notes
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