Compound: arbutin
SMILES: O1[C@@H](Oc2ccc(O)cc2)[C@H](O)[C@@H](O)[C@@H]([C@H]1CO)O
InChIKey: BJRNKVDFDLYUGJ-RMPHRYRLSA-N
Synonyms: arbutin, 497-76-7, Arbutoside, Ursin, beta-Arbutin, Uvasol, p-Hydroxyphenyl beta-D-glucoside, Arbutinum, 4-Hydroxyphenyl-beta-D-glucopyranoside, Hydroquinone-O-beta-D-glucopyranoside, Hydroquinone glucose, Hydroquinone-beta-D-glucopyranoside, hydroquinone O-beta-D-glucopyranoside, DTXSID7040152, (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol, C5INA23HXF, NSC-4036, beta-D-Glucopyranoside, 4-hydroxyphenyl, DTXCID5020152, CHEBI:18305, Bright Boost Cream, DRUGGIST Cream, skin brightening cream, HYDRO H, RefChem:28025, bright moisturizing cream, DRUGGIST Whitening Cream, DRUGGIST Brightening cream, Vitamin C Brightening Cream, Brightening Kojic Acid Cream, DRUGGIST Bright Boost Cream, 4-hydroxyphenyl-glucopyranoside, Tosowoong Mens Booster Repair Skin, ICEKING Freckle Removing Whitening Masque, Sooryehan Pure-Whitening Essential Starter, ICEKING Whitening Freckle Removing Essence, deep moisture and nourishment whitening cream, Dr Young 2p Brightening UV Sun Block SPF50 PA, ISAKNOX WHITE SYMPHONY BRIGHTENING EMULSION, ICEKING Freckle Removing Whitening Facial Cleanser, 207-850-3, 4-Hydroxyphenyl beta-D-glucopyranoside, p-Arbutin, p-Hydroxyphenyl beta-D-glucopyranoside, Hydroquinone beta-D-glucopyranoside, (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)tetrahydro-2H-pyran-3,4,5-triol, b-D-Glucopyranoside, 4-hydroxyphenyl, MFCD00016915, 4-Hydroxyphenyl-.beta.-D-glucopyranoside, CHEMBL232202, Arbutine, Arbutyne, Ursi, (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)tetrahydropyran-3,4,5-triol, Ericolin, NSC 4036, (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-oxidanylphenoxy)oxane-3,4,5-triol, CAS-497-76-7, Hydroquinone-glucose, Hydroquinone |A-D-glucopyranoside, SR-05000002157, UNII-C5INA23HXF, CCRIS 9273, -Arbutin, HSDB 7661, Arbutin CRS, NCGC00095599-01, Arbutin (Standard), EINECS 207-850-3, BRN 0089673, Spectrum_000786, Hydroquinone-D-glucoside, SpecPlus_000314, ARBUTIN [HSDB], Arbutin, >=98%, ARBUTIN [MI], ARBUTINUM [HPUS], ARBUTIN [MART.], Prestwick3_001026, Spectrum2_000662, Spectrum3_001233, Spectrum4_001474, Spectrum5_000147, Arbutin - Natural origin, ARBUTIN [WHO-DD], bmse000365, Arbutin - Synthetic origin, Arbutin (Uva, p-Arbutin), Arbutin, analytical standard, SCHEMBL36351, BSPBio_001211, BSPBio_002706, hydroquinone beta-D-glucoside, Hydroquinone-beta-D-glucoside, KBioGR_002047, KBioSS_001266, SPECTRUM300539, 5-17-07-00110 (Beilstein Handbook Reference), MLS002207046, DivK1c_006410, SPBio_000723, BPBio1_001333, MEGxp0_001504, orb1310578, orb3139364, HY-N0192R, KBio1_001354, KBio2_001266, KBio2_003834, KBio2_006402, KBio3_002206, HMS2098M13, HMS3715M13, P-Hydroxyphenyl beta -D-glucoside, HY-N0192, 4-Hydroxyphenyl-beta-glucopyranoside, Hydroquinone beta -D-glucopyranoside, Tox21_111509, Tox21_302428, BDBM50219502, CCG-38565, EBC-26392, s2263, 4-Hydroxyphenyl |A-D-glucopyranoside, AKOS015965305, Tox21_111509_1, DB11217, EA01844, EA31688, KS-5252, SDCCGMLS-0066538.P001, P-Hydroxyphenyl beta -D-glucopyranoside, SMP1_000028, NCGC00166076-02, NCGC00166076-03, NCGC00166076-04, NCGC00166076-07, NCGC00166076-09, NCGC00255705-01, AC-20183, beta -D-Glucopyranoside, 4-hydroxyphenyl, beta-D-Glucopyranoside, 4-hydroxyphenyl-, I(2)-D-Glucopyranoside, 4-hydroxyphenyl, SMR001233417, SY051904, A0522, AB00443586, HYDROQUINONE-.BETA.-D-GLUCOPYRANOSIDE, SW199492-2, C06186, 4-Hydroxyphenyl b-D-glucopyranoside, 9CI, 8CI, EN300-7388350, Arbutin, primary pharmaceutical reference standard, F105900, Q416446, SR-05000002157-2, SR-05000002157-4, BRD-K08037784-001-12-6, Arbutin, European Pharmacopoeia (EP) Reference Standard, 4E19B706-2013-4401-A1FC-A154DADF42B4, (2S,3R,4S,5S,6R)-2-(4-hydroxyphenoxy)-6-methylol-tetrahydropyran-3,4,5-triol, 7OQ
Theoretical properties:
molecular_formula: C12H16O7
molecular_weight: 272.25 g/mol
exact_mass: 272.08960285 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 7
rotatable_bond_count: 3
heavy_atom_count: 19
topological_polar_surface_area: 120 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Colorless elongated prisms from moist ethyl acetate
color: Colorless elongated prisms from moist ethyl acetate
solubility: ≥ 10g/100g
Descriptions:
pubchem: Hydroquinone O-beta-D-glucopyranoside is a monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage. It has a role as a plant metabolite and an Escherichia coli metabolite. It is a beta-D-glucoside and a monosaccharide derivative. It is functionally related to a hydroquinone.
chebi: A monosaccharide derivative that is  hydroquinone attached to a β-<small>D</small>-glucopyranosyl residue at position 4 via a glycosidic linkage.
chembl: ARBUTIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: β-Arbutin, also known by its International Nomenclature of Cosmetic Ingredients (INCI) name, arbutin, is a glycosylated derivative of hydroquinone. β-Arbutin is naturally present in the leaves and bark of a variety of plants, notably the bearberry plant, Arctostaphylos uva-ursi. Utilized as a biosynthetic active ingredient in topical treatments for skin lightening, β-arbutin is aimed at addressing hyperpigmentation issues. Its mechanism of action involves inhibiting the activity of tyrosinase, an essential enzyme for melanin synthesis in the human skin, thereby leading to a reduction in hyperpigmentation. It is important to distinguish β-arbutin from its structurally similar stereoisomer, α-arbutin, which exhibits similar effects in clinical applications.