(-)-spathulenol

General Material Information

Preferred name	(-)-spathulenol
Trivial Name	(4aS,7R,7aR)-1,1,7-trimethyl-4-methylidene-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-ol
Short Description	1H-cycloprop[e]azulen-7-ol, decahydro-1,1,7-trimethyl-4-methylene-, [1aS-(1aa,4aa,7b)]
Formula	C15 H24 O
CAS Number	77171-55-2
FDA UNII	TZZ5I978VX
xLogP3-AA	3.10 (est)
NMR Predictor	External link
Synonyms	1H- cycloprop[e]azulen-7-ol, decahydro-1,1,7-trimethyl-4-methylene-, [1aS-(1aa,4aa,7b)] (-)-ent- spathulenol ent- spathulenol (4aS,7R,7aR)-1,1,7-trimethyl-4-methylidene-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-ol

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Literature & References

	(4aS,7R,7aR)-1,1,7-trimethyl-4-methylidene-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-ol
NIST Chemistry WebBook:	Search Inchi
Pubchem (cid):	6432706
Pubchem (sid):	10535467
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Publications by PubMed
Volatile Oils from the Aerial Parts of Eremophila maculata and Their Antimicrobial Activity.
Airborne Antituberculosis Activity of Eucalyptus citriodora Essential Oil.
Terpene constituents of the leaves of five Vietnamese species of Clausena (Rutaceae).
Comparison of the volatile oil composition of three Atalantia species.
Chemical composition of essential oils from the leaves and stem barks of Vietnamese species of Polyalthia harmandii, Polyalthia jucunda and Polyalthia thorelii.
Chemical composition and general toxicity of essential oils extracted from the aerial parts of Artemisia armeniaca Lam. and A. incana (L.) Druce growing in Iran.
Comparative analysis of the essential oil composition of Murraya paniculata and M. exotica.
Essential oils composition of croton species from the Amazon.
Chemical composition and insecticidal activity of plant essential oils from Benin against Anopheles gambiae (Giles).
The seasonal variation of the chemical composition of essential oils from Porcelia macrocarpa R.E. Fries (Annonaceae) and their antimicrobial activity.
Variability of the root essential oils of Seseli rigidum Waldst. & Kit. (Apiaceae) from different populations in Serbia.
Study on Gas Chromatography-Mass Spectrometry Fingerprint of Acanthopanax brachypus.
Nematicidal activity of the essential oil of Rhododendron anthopogonoides aerial parts and its constituent compounds against Meloidogyne incognita.
Identification of repellent and insecticidal constituents of the essential oil of Artemisia rupestris L. aerial parts against Liposcelis bostrychophila Badonnel.
Genotoxic effects of Campomanesia xanthocarpa extracts on Allium cepa vegetal system.
GC and GC-MS analysis of the essential oil of Nepeta cilicica Boiss. ex Benth. from Lebanon.
[Chemical constituents of stems and leaves of Salvia yunnanensis and their anti-angiogeneic activities].
Compounds from the Fruits of the Popular European Medicinal Plant Vitex agnus-castus in Chemoprevention via NADP(H):Quinone Oxidoreductase Type 1 Induction.
Analysis of the essential oil of Dipsacus japonicus flowering aerial parts and its insecticidal activity against Sitophilus zeamais and Tribolium castaneum.
Chemical composition of essential oils and in vitro antioxidant activity of fresh and dry leaves crude extracts of medicinal plant of Lactuca Sativa L. native to Sultanate of Oman.
Chemical composition and antimicrobial activity of essential oils from Chromolaena laevigata during flowering and fruiting stages.
Nudibaccatumone, a trimer comprising a phenylpropanoid and two sesquiterpene moieties from Piper nudibaccatum.
Essential oils from five species of Annonaceae from Vietnam.
Chemical composition of Hypericum richeri subsp. grisebachii essential oil from Croatia.
Hirtinone, a Novel cycloartane-type triterpene and other compounds from Trichilia hirta L. (Meliaceae).
Chemical diversity among the essential oils of wild populations of Stachys lavandulifolia VAHL (Lamiaceae) from Iran.
GC-MS analysis of insecticidal essential oil of flowering aerial parts of Saussurea nivea Turcz.
Volatile oil constituents of different parts of Artemisia chamaemelifolia and the composition and antibacterial activity of the aerial parts of A. turcomanica from Iran.
Composition of the essential oils from Peucedanum cervaria and P. alsaticum growing wild in the urban area of Vienna (Austria).
Chemotaxonomic and micromorphological traits of Satureja montana L. and S. subspicata Vis. (Lamiaceae).
Chemotaxonomical markers in essential oil of Murraya koenigii.
Essential oil and other constituents from Magnolia ovata fruit.
Metabolism by grasshoppers of volatile chemical constituents from Mangifera indica and Solanum paniculatum leaves.
Study on the volatile oil contents of Annona glabra L., Annona squamosa L., Annona muricata L. and Annona reticulata L., from Vietnam.
Chemical composition of the essential oils of Centaurea formanekii and C. orphanidea ssp. thessala, growing wild in Greece.
Chemical composition, antimicrobial, antioxidant and cytotoxic activity of the essential oil from the leaves of Acanthopanax leucorrhizus (Oliv.) Harms.
Differences in the volatile compositions of ginseng species (Panax sp.).
Constituents and antimicrobial activity of the essential oils from flower, leaf and stem of Helichrysum armenium.
Chemical composition and antibacterial activity of the essential oil of Espeletia nana.
Chemical classification of the essential oils of the Iranian Salvia species in comparison with their botanical taxonomy.
Culture conditions and salt effects on essential oil composition of sweet marjoram (Origanum majorana) from Tunisia.
Fragrant volatile oil composition of Nutmeg Geranium (Pelargonium × fragrans Willd.) from India.
Velamo do campo: its volatile constituents, secretory elements, and biological activity.
Evaluation of the antinociceptive, anti-inflammatory and gastric antiulcer activities of the essential oil from Piper aleyreanum C.DC in rodents.
Antioxidant activities and essential oil composition of Herba Artemisiae Scopariae from China.
Essential oil from the leaves of Annona vepretorum: chemical composition and bioactivity.
Chemical composition and in vitro antimicrobial activity of the essential oil of Cyclotrichium leucotrichum from Iran.
Chemical composition, antimicrobial, antiradical and anticholinesterase activity of the essential oil of Pulicaria stephanocarpa from Soqotra.
Composition of the essential oil of Pogostemon travancoricus var. travancoricus.
Correlation between chemical composition and antibacterial activity of essential oils from fifteen Eucalyptus species growing in the Korbous and Jbel Abderrahman arboreta (North East Tunisia).
Composition of the volatile oils of two Anthemis L. taxa from Turkey.
Chemical composition and antioxidant activity of the essential oil of Tabernaemontana catharinensis A. DC. leaves.
Phytotoxic activity in Flourensia campestris and isolation of (--)-hamanasic acid A as its active principle compound.
Volatile constituents of two species of Protium from the Atlantic rainforest in the state of Pernambuco, Brazil.
Sedative effects of essential oils obtained from Baccharis uncinella.
Toxicity of Rhododendron anthopogonoides essential oil and its constituent compounds towards Sitophilus zeamais.
Chemical and allelopathic analyses of essential oils of Prangos pabularia Lindl. from Iran.
Acaricidal, insecticidal, and larvicidal efficacy of fruit peel aqueous extract of Annona squamosa and its compounds against blood-feeding parasites.
Chemical composition and antimicrobial activity of essential oil of Achillea cretica L. (Asteraceae) from Turkey.
Volatile components from aerial parts of Centaurea gracilenta and C. ovina ssp. besserana growing wild in Bulgaria.
Chemical composition, antioxidant and antimicrobial activity of the extracts of the flowers of the Chinese plant Chimonanthus praecox.
[Chemical composition of essential oils from leaves of Helicteres guazumifolia (Sterculiaceae), Piper tuberculatum (Piperaceae), Scoparia dulcis (Arecaceae) and Solanum subinerme (Solanaceae) from Sucre, Venezuela].
Phytochemical analysis and in vitro antimicrobial and free-radical-scavenging activities of the essential oils from Euryops arabicus and Laggera decurrens.
Composition and antifungal activity of the essential oil from the rhizome and roots of Ferula hermonis.
Chemical Compositionand Anti-acetyl cholinesterase Activity of Flower Essential Oils of Artemisiaannuaat Different Flowering Stage.
GC/MS analysis and analgesic effect of the essential oil of Matricaria pubescens from Algeria.
Volatile constituent distribution of Prangos coryombosa Boiss at two stages of growth.
Characterisation of the essential oil of Nepeta glomerata Montbret et Aucher ex Bentham from Lebanon and its biological activities.
Essential oil composition of endemic Tanacetum zahlbruckneri (Nab.) and Tanacetum tabrisianum (Boiss.) Sosn. and Takht. from Turkey.
Anti-inflammatory diterpene from Thyrsanthera suborbicularis.
Chemical composition of the essential oil of Croton gossypiifolius from Venezuela.
Variation in volatile leaf oils of seven eucalyptus species harvested from Zerniza arboreta (Tunisia).
Variation in volatile leaf oils of five Eucalyptus species harvested from Jbel Abderrahman arboreta (Tunisia).
Eucalyptus oleosa essential oils: chemical composition and antimicrobial and antioxidant activities of the oils from different plant parts (stems, leaves, flowers and fruits).
Caryophyllene oxide-rich essential oils of Lithuanian Artemisia campestris ssp. campestris and their toxicity.
Chemical constituents and larvicidal activity of Hymenaea courbaril fruit peel.
Chemical composition and mosquito larvicidal activities of Salvia essential oils.
Chemical composition and cytotoxicity of oils and eremophilanes derived from various parts of Eremophila mitchellii Benth. (Myoporaceae).
Phytochemical analysis and antioxidant activity of Hyssopus officinalis L. from Iran.
Chemical composition and antimicrobial activity of essential oils from Centaurea pannonica and C. jacea.
Composition of essential oils in subterranean organs of three species of Valeriana L.
Essential oil composition of leaves of Stachys yemenensis obtained by supercritical CO₂.
Chemical composition, seasonal variation, and biosynthetic considerations of essential oils from Baccharis microdonta and B. elaeagnoides (Asteraceae).
Identification of spathulenol in Salvia mirzayanii and the immunomodulatory effects.
Chemical composition and antimicrobial activity of the essential oils from Cleome spinosa.
Chemical composition and toxicity against Sitophilus zeamais and Tribolium castaneum of the essential oil of Murraya exotica aerial parts.
Volatile profiles of Artemisia alba from contrasting serpentine and calcareous habitats.
Chemical composition of the essential oil and hexane extract of Salvia chionantha and their antioxidant and anticholinesterase activities.
Chemical composition and larvicidal activity against Aedes aegypti larvae of essential oils from four Guarea species.
[Analysis of the chemical constituents of essential oil from the leaves of Callicarpa integerrima].
Essential oil composition and variability of Hypericum perforatum from wild populations of northern Turkey.
Variation in volatile leaf oils of eleven eucalyptus species harvested from korbous arboreta (Tunisia).
Anti-inflammatory activity of essential oil from leaves of Myrciaria tenella and Calycorectes sellowianus.
Antifungal activity of extracts of some plants used in Brazilian traditional medicine against the pathogenic fungus Paracoccidioides brasiliensis.
Isolation and structure determination of one new metabolite isolated from the red fermented rice of Monascus purpureus.
Antimicrobial activity and chemical composition of endemic Centaurea cariensis subsp. niveo-tomentosa.
Antiprotozoal, schistosomicidal, and antimicrobial activities of the essential oil from the leaves of Baccharis dracunculifolia.
Variation in volatile leaf oils of 13 Eucalyptus species harvested from Souinet arboreta (Tunisia).
Extraction, separation and isolation of volatiles from Vitex agnus-castus L. (Verbenaceae) wild species of Sardinia, Italy, by supercritical CO2.
Composition and anti-wood-decay fungal activities of the leaf essential oil of Machilus philippinensis from Taiwan.
Chemical variability, antifungal and antioxidant activity of Eucalyptus camaldulensis essential oil from Sardinia.
Volatile components of aerial parts of Centaurea nigrescens and C. stenolepis growing wild in the Balkans.
Two new terpenoids from Trichilia quadrijuga (Meliaceae).
Variation in volatile leaf oils of twelve eucalyptus species harvested from Hajeb Layoun arboreta (Tunisia).
Chemotypes of Pistacia atlantica leaf essential oils from Algeria.
Croton sonderianus essential oil samples distinctly affect rat airway smooth muscle.
Structure-activity relationships of aromadendranes in uterus-relaxant activity.
Genotoxic activity of Eucalyptus globulus essential oil in Aspergillus nidulans diploid cells.
Content and composition of the essential oil of Chamomilla recutita (L.) Rauschert from some European countries.
[Study on the volatile oil of Murraya exotica].
Gastroprotective effect and cytotoxicity of abietane diterpenes from the Chilean Lamiaceae Sphacele chamaedryoides (Balbis) Briq.
Chemical composition of endemic Centaurea austro-anatolica and studies of its antimicrobial activity against multi-resistant bacteria.
Composition and biological activity of essential oils from Protium confusum.
In vitro study of antibacterial activity on multi-resistant bacteria and chemical composition of the chloroform extract of endemic Centaurea drabifolia subsp. cappadocica.
Anti-leishmanial lindenane sesquiterpenes from Hedyosmum angustifolium.
Differential acetyl cholinesterase inhibition by volatile oils from two specimens of Marlierea racemosa (Myrtaceae) collected from different areas of the Atlantic Rain Forest.
Constituents of the leaves of Magnolia ovata.
Chemical variation of the essential oil of Prangos uloptera DC. at different stages of growth.
Temperature-dependent release of volatile organic compounds of eucalypts by direct analysis in real time (DART) mass spectrometry.
Secondary metabolites and cytotoxic activities from the stem bark of Zanthoxylum nitidum.
Antimicrobial activity and chemical composition of Senecio sandrasicus on antibiotic resistant staphylococci.
Chemical composition and antibacterial activity of essential oils of Eugenia species.
Antiulcerogenic and anti-inflammatory activities of the essential oil from Pterodon emarginatus seeds.
Chemical composition, antimicrobial and antioxidant activities of Centaurea ensiformis Hub.-Mor. (Asteraceae), a species endemic to Mugla (Turkey).
Chemical composition and in vitro antimicrobial activity of the essential oils of two Helichrysum species from Tanzania.
[Chemical constituents from the seed of Chimonanthus praecox extracted by supercritical carbon dioxide].
Leaf essential oil composition of three species of Myrcianthes from Monteverde, Costa Rica.
[Studies on expectorant compounds in volatile oil from root and rhizome of Aster tataricus].
Variability of two essential oils of Kundmannia sicula (L.) DC., a traditional Algerian medicinal plant.
Antifungal activity of Heterothalamus alienus metabolites.
Composition of Eucalyptus camaldulensis volatiles using direct thermal desorption coupled with comprehensive two-dimensional gas chromatography-time-of-flight-mass spectrometry.
Phytochemical investigation on leaf extract of Cordia salicifolia Cham.
Antifungal activity of essential oils of Croton species from the Brazilian Caatinga biome.
Composition, and anti-inflammatory and antioxidant activities of the volatile oil from the fruit peel of Garcinia brasiliensis.
Spasmolytic effect of constituents from Lepechinia caulescens on rat uterus.
Studies on the antioxidant activity of the essential oil and methanol extract of Marrubium globosum subsp. globosum (lamiaceae) by three different chemical assays.
Flavaglines and triterpenoids from the leaves of Aglaia forbesii.
Essential oil of trees of the genus Ocotea (Lauraceae) in Costa Rica. I. Ocotea brenesii.
Composition, antimicrobial activity and cytotoxicity of essential oils from Aristolochia mollissima.
Diterpenoids and flavonoids from the fruits of Vitex agnus-castus and antioxidant activity of the fruit extracts and their constituents.
Antimicrobial activity of the essential oil and extracts of Cordia curassavica (Boraginaceae).
Comparison of composition and antifungal activity of Artemisia argyi Lévl. et Vant inflorescence essential oil extracted by hydrodistillation and supercritical carbon dioxide.
Essential oil of the Persian sage, Salvia rhytidea Benth.
Analysis of the essential oil composition of eight Anthemis species from Greece.
GC-MS fingerprint of Pogostemon cablin in China.
Study on the antiinflammatory activity of essential oil from leaves of Cinnamomum osmophloeum.
Gaudichanolides A and B, clerodane diterpenes from Baccharis gaudichaudiana.
Isolation and identification of mosquito bite deterrent terpenoids from leaves of American (Callicarpa americana) and Japanese (Callicarpa japonica) beautyberry.
Gastric antiulcer and anti-inflammatory activities of the essential oil from Casearia sylvestris Sw.
Comparison of the volatile composition of Stachys persica Gmel. and Stachys byzantina C. Koch. oils obtained by hydrodistillation and steam distillation.
Caesaldecan, a cassane diterpenoid from the leaves of Caesalpinia decapetala.
Phytochemical analysis and in vitro antimicrobial activity of two Satureja species essential oils.
Screening of chemical composition and antifungal and antioxidant activities of the essential oils from three Turkish artemisia species.
Bioactive constituents of Artemisia monosperma.
Effect of magnesium on essential oil formation of genetically transformed and non-transformed chamomile cultures.
Geranyl N-dimethylallylanthranilate, a new compound from Esenbeckia yaaxhokob.
Chemical and biological evaluation of the essential oils of different Melaleuca species.
Composition and anti-plasmodial activities of essential oils from some Cameroonian medicinal plants.
A new furanoid diterpene from Caesalpinia pulcherrima.
Composition and antimicrobial activity of the essential oils from invasive species of the Azores, Hedychium gardnerianum and Pittosporum undulatum.
Sesquiterpenes from Achillea pannonica Scheele.
Composition and antibacterial activity of the essential oil of Satureja parnassica subsp parnassica.
[GC-MS analysis and inhibitory activity of the essential oil extracted from the leaves of Lindera communis].
Chemical analysis and antifungal activity of the essential oil of Calea clematidea.
Phytotoxicity and volatile constituents from leaves of Callicarpa japonica Thunb.
Effect of drying method on the volatiles in bay leaf (Laurus nobilis L.).
Essential oil composition of sea fennel (Crithmum maritimum) form Turkey.
Comparison of the essential oils of Glehnia littoralis from Northern and Southern Japan.
Eucalyptus camaldulensis: volatiles from immature flowers and high production of 1,8-cineole and beta-pinene by in vitro cultures.
3-Acetoxyspathulenol, a new aromadendrane-type natural product from the soft Coral Parerythropodium fulvum.
Composition and antimicrobial activity of the essential oil of Baccharis notosergila.
Bioactive constituents of Conyza albida.
Genetic diversity of Ocimum gratissimum L. based on volatile oil constituents, flavonoids and RAPD markers.
A study of the production of essential oils in chamomile hairy root cultures.
The steam volatile oil of Wollemia nobilis and its comparison with other members of the Araucariaceae (Agathis and Araucaria).
Terpenoids from Salvia sclarea.
Cytotoxic constituents of Baccharis gaudichaudiana.
Plant anticancer agents, L. cytotoxic triterpenes from Sandoricum koetjape stems.
Isolation and identification of cotton synomones mediating searching behavior by parasitoidCampoletis sonorensis.
Composition of essential oils of Laurus nobilis, L. nobilis var. angustifolia and Laurus azorica.
[Substances first isolated from the essential oils of two artemisia-species, 1. Spathulenol, an azulenogenic C15-alcohol (author's title)].

Other Information

(IUPAC):	Atomic Weights of the Elements 2011 (pdf)
Videos:	The Periodic Table of Videos
tgsc:	Atomic Weights use for this web site
(IUPAC):	Periodic Table of the Elements
HMDB (The Human Metabolome Database):	HMDB36420
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	220.35548400879
Boiling Point	295 to 297°C @ 760 mm Hg
Vapor Pressure	0.00014 mmHg @ 25 °C
Flash Point TCC Value	123.9 °C TCC
logP (o/w)	4.455 est
Solubility
alcohol	Yes
water, 12.44 mg/L @ 25 °C (est)	Yes
water	No

Organoleptic Properties

Odor Type: Honey
honey
General comment	At 100.00 %. honey

Occurrences

Safety Information

Safety information


Hazards identification

Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements

Pictogram

Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
natural substances and extractives
Recommendation for (-)-spathulenol usage levels up to:
	not for fragrance use.

Recommendation for (-)-spathulenol flavor usage levels up to:
	not for flavor use.

Safety references

EPI System: View

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :6432706

National Institute of Allergy and Infectious Diseases:Data

(4aS,7R,7aR)-1,1,7-trimethyl-4-methylidene-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-ol

Chemidplus:0077171552