2-Butenoic acid, 2-methyl-, (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-1a,2,5,5a,6,9,10,10a-octahydro-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1H-2,8a-methanocyclopenta[a]cyclopropa[e]cyclodecen-6-yl ester, (2Z)-, 98%, 98%

cas: 75567-37-2 — see every product listed under this CAS number, including other names

2-Butenoic acid, 2-methyl-, (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-1a,2,5,5a,6,9,10,10a-octahydro-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1H-2,8a-methanocyclopenta[a]cyclopropa[e]cyclodecen-6-yl ester, (2Z)-, 98%, 98% (CAS 75567-37-2) is a chemical reagent available from Chemat. Available pack sizes: 1mg, 5mg, 10mg, 25mg, 50mg. Offered by: Chemat.

• 2D
• 3D

Ingenol mebutate is a tetracyclic diterpenoid ester obtained by formal condensation of the carboxy group of (2Z)-2-methylbut-2-enoic (angelic) acid with the 3-hydroxy group of ingenol. Used for the topical treatment of actinic keratosis. It has a role as an antineoplastic agent. It is a carboxylic ester, a cyclic terpene ketone and a tetracyclic diterpenoid. It is functionally related to an angelic acid and an ingenol.

Source: ChEBI

Identity

Molecular formula	C25H34O6
Molecular weight	430.5 g/mol
IUPAC name	[(1S,4S,5S,6R,9S,10R,12R,14R)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxo-4-tetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dienyl] (Z)-2-methylbut-2-enoate
InChIKey	VDJHFHXMUKFKET-WDUFCVPESA-N
SMILES	C/C=C(/C)\C(=O)O[C@H]1C(=C[C@@]23[C@@]1([C@@H](C(=C[C@H](C2=O)[C@H]4[C@H](C4(C)C)C[C@H]3C)CO)O)O)C

Computed by PubChem (NCBI)

Synonyms: Ingenol mebutate, Ingenol 3-angelate, 3-Ingenyl angelate, 3-Angeloylingenol, Ingenol-3-angelate, mebutate d'ingenol, mebutato de ingenol, Euphorbia factor H1, Euphorbia factor An1, ingenoli mebutas

Isomers (same molecular formula)

(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one C₂₅H₃₄O₆

(1S,2S,4R,6S,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one C₂₅H₃₄O₆

(1S,2S,4R,6R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one C₂₅H₃₄O₆

[(6S,8S,9S,10R,11S,13S,14S,17R)-11-hydroxy-17-(2-hydroxyacetyl)-6,10,13-trimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl] propanoate C₂₅H₃₄O₆

[2-[(6S,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] propanoate C₂₅H₃₄O₆

(1S,2S,4R,8S,9S,11S,12S,13R)-6-deuterio-6-(1,1,2,2,3,3,3-heptadeuteriopropyl)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one C₂₅H₃₄O₆

(4R,8'S,9'S,10'R,11'S,13'S,14'S)-2-ethoxy-11'-hydroxy-2,10',13'-trimethylspiro[1,3-dioxane-4,17'-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene]-3',5-dione C₂₅H₃₄O₆

(4aR,4bS,5S,6aS,7aR,10aR,11aS,11bS)-5-hydroxy-7a-(hydroxymethyl)-4a,6a-dimethyl-9-propyl-5,6,10a,11,11a,11b,12,13-octahydro-4bH-chryseno[2,3-d][1,3]dioxole-2,7-dione C₂₅H₃₄O₆

[2-[(8'S,10'S,13'S,14'S,17'R)-17'-hydroxy-10',13'-dimethylspiro[1,3-dioxolane-2,3'-2,4,7,8,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene]-17'-yl]-2-oxoethyl] acetate C₂₅H₃₄O₆

methyl (2E)-2-[(8R,9S,10R,13S,14S,17S)-2'-methoxy-2',13-dimethyl-3-oxospiro[1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-17,5'-1,3-dioxolane]-4'-ylidene]acetate C₂₅H₃₄O₆

(1S,2S,4R,8S,9S,11S,12S,13R)-15,17,19,19-tetradeuterio-8-(2,2-dideuterio-2-hydroxyacetyl)-11-hydroxy-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one C₂₅H₃₄O₆

[2-[(8S,9S,10R,13S,14S,17R)-3-ethoxy-17-hydroxy-10,13-dimethyl-11-oxo-2,7,8,9,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate C₂₅H₃₄O₆