| Identification | Back Directory | [Name]
(1S)-7-Isopropylidene-1,2,3,3aα,4,5,6,7,8,8aβ-decahydro-1β-hydroxy-1-methyl-4-methyleneazulen-6-one | [CAS]
102130-90-5 | [Synonyms]
Isoprocurcumenol
6(1H)-Azulenone,octahydro-1-hydroxy-1-methyl-4-methylene-7-(1-methylethylidene)-, (1S,3aR,8aS)-
(1S)-7-Isopropylidene-1,2,3,3aα,4,5,6,7,8,8aβ-decahydro-1β-hydroxy-1-methyl-4-methyleneazulen-6-one
[1S-(1alpha,3abeta,8aalpha)]-Octahydro-1-hydroxy-1-methyl-4-methylene-7-(1-methylethylidene)-6(1H)-azulenone | [Molecular Formula]
C15H22O2 | [MDL Number]
MFCD31810158 | [MOL File]
102130-90-5.mol | [Molecular Weight]
234.33 |
| Chemical Properties | Back Directory | [form ]
Solid | [color ]
White to off-white | [Cosmetics Ingredients Functions]
SKIN CONDITIONING - MISCELLANEOUS
SKIN PROTECTING
HAIR CONDITIONING | [InChI]
InChI=1S/C15H22O2/c1-9(2)12-8-13-11(5-6-15(13,4)17)10(3)7-14(12)16/h11,13,17H,3,5-8H2,1-2,4H3/t11-,13-,15-/m0/s1 | [InChIKey]
ITIGZFMSPAFZAE-WHOFXGATSA-N | [SMILES]
[C@@]1(O)(C)[C@]2([H])[C@]([H])(C(=C)CC(=O)/C(=C(\C)/C)/C2)CC1 |
| Hazard Information | Back Directory | [Uses]
Isoprocurcumenol is a guaiane type sesquiterpene, that can be isolated from Curcuma comosa. Isoprocurcumenol can activate EGFR signaling. Isoprocurcumenol increases the phosphorylation of ERK and AKT. Isoprocurcumenol promotes the proliferation of keratinocytes[1][2][3]. | [Definition]
ChEBI: (1alpha,4beta,5beta)-4-Hydroxy-7(11),10(14)-guaiadien-8-one is a sesquiterpenoid. | [IC 50]
ERK; Akt | [References]
[1] Qu Y, et al. Sesquiterpenes from Curcuma comosa. J Nat Med. 2009 Jan;63(1):102-4. DOI:10.1007/s11418-008-0282-8
[2] Anuchapreeda S, et al. Cytotoxicity and inhibition of leukemic cell proliferation by sesquiterpenes from rhizomes of Mah-Lueang (Curcuma cf. viridiflora Roxb.). Bioorg Med Chem Lett. 2018 Feb 1;28(3):410-414. DOI:10.1016/j.bmcl.2017.12.029
[3] Kwon PK, et al. Isoprocurcumenol Supports Keratinocyte Growth and Survival through Epidermal Growth Factor Receptor Activation. Int J Mol Sci. 2021 Nov 22;22(22):12579. DOI:10.3390/ijms222212579 |
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