Compound Summary

General Compound Information

Galaxolide

Description
Galaxolide is an organic heterotricyclic compound that is 1,3,4,6,7,8-hexahydrocyclopenta[g]isochromene substituted by methyl groups at positions 4, 6, 6, 7, 8 and 8 respectively. It is a synthetic musk used as a fragrance in cosmetics. It has a role as a fragrance. It is a member of isochromenes and an organic heterotricyclic compound.
Synonyms
Galaxolide;  1222-05-5;  Abbalide;  Galoxolide;  4,6,6,7,8,8-Hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]isochromene;
FlavorDB ID
4400
PUBCHEM ID
Molecular Weight
258.4
Molecular Formula
C18H26O
Openeye Can Smiles
CC1COCC2=CC3=C(C=C12)C(C(C3(C)C)C)(C)C
IUPAC Inchikey
ONKNPOPIGWHAQC-UHFFFAOYSA-N
Compound Classification
Compound classification information is not available!
Compound Quality
CATEGORY QUALITY THRESHOLD OCCURENCE REFERENCE
smell Perfume, Musk, flowery, soapy water details
smell Perfume, Musk, flowery, soapy 1.936e-2 µmol/L water details
Compound Toxicity and Food Additive Safety (OFAS)
Toxicity Summary
Link to the Distributed Structure-Searchable Toxicity (DSSTox) Database
IDENTIFICATION AND USE: Galaxolide (HHCB) is an almost colorless viscous liquid. It is a synthetic, artificial musk fragrance, which is used as a laundry detergent fragrance, as well as an ingredient in perfumes, soaps, and cosmetics. HUMAN STUDIES: No irritation was observed in any of the 42 subjects tested in human repeated insult patch test even after repeated occlusive applications of undiluted material. High concentrations of HHCB can affect steroidogenesis in vitro using the H295R cell line. HHCB was not genotoxic in the micronucleus test with human lymphocytes in vitro in the presence and absence of metabolic activation. ANIMAL STUDIES: HHCB was added to the diet of rats at levels calculated to result in mean daily doses of 5, 15, 50 or 150 mg HHCB/kg. On completion of the 90-day treatment period, three males and three females from the high dose and control groups were maintained for a treatment free period of 4 weeks. No adverse effects were revealed from clinical examination or following extensive histopathological examinations. There were no significant findings at any dose level. Developmental study in rats described axial skeletal malformations at 500 mg/kg per day. In rats chronically exposed to HHCB (35 mg/kg), reduced weight at birth at F1, induction of CYP2B and CYP3A and a slight increase in HDL-cholesterol in males was reported. In a Xenopus laevis metamorphosis study, developmental acceleration on day 14, together with hypertrophy of the thyroid follicular epithelium in tadpoles, suggested a possible agonistic effect of HHCB. When HHCB was injected i.p. into trout at a dose of 3.64 mg/kg, it caused inhibition of E2-induced vitellogenin production. The interaction of HHCB with the estrogen receptor (ER), androgen receptor (AR), and progesterone (PR) receptor, using sensitive and specific reporter gene cell lines was assessed. HHCB was found to be an antagonist toward the ERbeta, AR and PR. HHCB was not genotoxic when tested in Salmonella typhimurium strains TA97, TA98, TA100 and TA102 with or without metabolic activation. ECOTOXICITY STUDIES: In Dreissena polymorpha HHCB induced significant increases in lipid peroxidation and protein carbonyl levels. Moreover, significant increases in DNA strand breaks were caused by exposure to the highest concentrations HHCB, but no fixed genetic damage was observed. The mRNA expression levels of the four representative protein-coding genes (HSP70, CRT, cyPA, TCTP) were examined in earthworm Eisenia fetida exposed to HHCB. The results indicated that HSP70 and CRT genes expression patterns might be potential early molecular biomarkers for predicting the harmful exposure level and ecotoxicological effects of HHCB. In another study in earthworms, superoxide dismutase and catalase appeared to be the most responsive biomarkers of oxidative stress caused by HHCB.
Source: DrugBank or Hazardous Substances Data Bank (HSDB)
Receptors
Receptor information of this compound is not available!
Consensus Spectra
Spectrum Type Spectrum View Description Polarity
Experimental LCMS view LCMS_Positive positive