Page last updated: 2024-12-05

hexadecanolide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Hexadecanolide, also known as palmitolactone, is a naturally occurring macrocyclic lactone with a 16-carbon ring. It is found in various plants, including the leaves of the sweet basil and in animal sources like honeybees. The compound exhibits a variety of biological activities, including antibacterial, antifungal, and anti-inflammatory effects. Its synthesis has been achieved through various methods, including the Baeyer-Villiger oxidation of palmitic acid and ring-closing metathesis of unsaturated fatty acids. Research on hexadecanolide focuses on its potential applications in medicine, agriculture, and cosmetics, exploring its antimicrobial properties, insecticidal effects, and its potential as a fragrance component. '

hexadecanolide: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID7984
CHEMBL ID3189021
CHEBI ID179821
SCHEMBL ID111372
MeSH IDM0573016

Synonyms (55)

Synonym
CHEBI:179821
nsc-33546
16-hexadecanolactone
juniperic acid, lactone
juniperic acid lactone
oxacycloheptadecan-2-one
109-29-5
cyclohexadecanolide
hexadecanoic acid, .omicron.-lactone
1,16-hexadecanolide
hexadecanolide
dihydroambrettolide
NSC33546 ,
brn 0148631
1,16-hexadecalactone
nsc 33546
ai3-37208
16-hydroxyhexadecanoic acid lactone
hexadecanoic acid, 16-hydroxy-, omicron-lactone
1,16-hexadecanolactone
einecs 203-662-0
16-hexadecanolide
16-hexadecanolide, 97%
H1219
1-oxacycloheptadecan-2-one
5-17-09-00108 (beilstein handbook reference)
64e2ho00c7 ,
unii-64e2ho00c7
hexadecanolactone
LMFA07040054
NCGC00256920-01
dtxcid2027622
dtxsid4047622 ,
cas-109-29-5
tox21_302621
CCG-36363
FT-0607252
SCHEMBL111372
hexadecanolactone [inci]
hexadecanoic acid, 16-hydroxy-, o-lactone
hexadecano-16-lactone
hexadecanoic acid, 16-hydroxy-, .omicron.-lactone
hexadecanolide, >=98%, stabilized
CHEMBL3189021
mfcd00039668
J-002261
16-hexadecanolide, analytical standard
16-hexadecanolide, reference material
F10387
Q21099108
SY038613
2-oxacyclo-heptadecanone
AS-81214
CS-0068061
AKOS040744516

Research Excerpts

Overview

Hexadecanolide is a member of the fragrance structural group macrocyclic lactone and lactide derivatives.

ExcerptReferenceRelevance
"Hexadecanolide is a member of the fragrance structural group macrocyclic lactone and lactide derivatives."( Fragrance material review on hexadecanolide.
Api, AM; Letizia, CS; McGinty, D, 2011
)
1.38

Bioavailability

ExcerptReferenceRelevance
" Deuterated drug molecules (heavy drugs) become novel as well as popular because of better stability and bioavailability compared with their hydrogen analogs."( A facile synthesis of 5,5-dideutero-4-dimethyl(phenyl)silyl-6-undecyl-tetrahydropyran-2-one as a deuterium labeled synthon for (-)-tetrahydrolipstatin and (+)-δ-hexadecanolide.
Chowdhury, R; Ghosh, SK; Mukhopadhyay, S; Wagh, SJ, 2013
)
0.59
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
macrolideA macrocyclic lactone with a ring of twelve or more members derived from a polyketide.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (8)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency76.95880.003041.611522,387.1992AID1159552
estrogen nuclear receptor alphaHomo sapiens (human)Potency3.08990.000229.305416,493.5996AID743075
vitamin D (1,25- dihydroxyvitamin D3) receptorHomo sapiens (human)Potency61.65240.023723.228263.5986AID743241
thyroid stimulating hormone receptorHomo sapiens (human)Potency51.43500.001628.015177.1139AID1259395
activating transcription factor 6Homo sapiens (human)Potency21.87510.143427.612159.8106AID1159516
v-jun sarcoma virus 17 oncogene homolog (avian)Homo sapiens (human)Potency48.97220.057821.109761.2679AID1159528
Histone H2A.xCricetulus griseus (Chinese hamster)Potency50.47720.039147.5451146.8240AID1224845
heat shock protein beta-1Homo sapiens (human)Potency58.20360.042027.378961.6448AID743228
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (4)

Assay IDTitleYearJournalArticle
AID1224817Assays to identify small molecules inhibitory for eIF4E expression2015Chemistry & biology, Jul-23, Volume: 22, Issue:7
Internal Ribosome Entry Site-Based Bicistronic In Situ Reporter Assays for Discovery of Transcription-Targeted Lead Compounds.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's3 (60.00)24.3611
2020's2 (40.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 33.45

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index33.45 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index37.86 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (33.45)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (20.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other4 (80.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]