leerall (lyral)

General Material Information

Preferred name	leerall (lyral)
Trivial Name	lyral (IFF)
Short Description	4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde
Formula	C13 H22 O2
CAS Number	31906-04-4
Deleted CAS Number	56493-02-8
ECHA Number	250-863-4
FDA UNII	QUE43B9Z2Q
Nikkaji Number	J68.877K
Beilstein Number	2046455
MDL	MFCD00019423
xLogP3-AA	1.70 (est)
NMR Predictor	External link
Synonyms	3 and 4-(4-hydroxy-4-methyl pentyl) cyclohex-3-ene-1-carbaldehyde 3 and 4-(4-hydroxy-4-methyl pentyl)-3-cyclohexene-1-carboxaldehyde 3 and 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde 3 and 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde 3-cyclohexene-1-carboxaldehyde, 4-(4-hydroxy-4-methylpentyl)- 3-Cyclohexene-1-carboxaldehyde, 4-(4-hydroxy-4-methylpentyl)- 4-(4-hydroxy-4-methyl pentyl) cyclohex-3-ene-1-carbaldehyde 4-(4-hydroxy-4-methyl pentyl)-3-cyclohexene-1-carboxaldehyde 4-(4-hydroxy-4-methylpentyl)-1-cyclohex-3-enecarboxaldehyde 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehye 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene carbaldehyde 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde 4-(4-hydroxy-4-methylpentyl)cyclohex-3-enecarbaldehyde 4-(4-Hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde 4-(4-Hydroxy-4-methylpentyl)-3-cyclohexenecarboxaldehyde 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde 4-(4-Methyl-4-hydroxyamyl)cyclohex-3-ene carboxaldehyde 4,4-hydroxymethyl pentyl cyclohexene carbaldehyde cyclohexal hydroxyisohexyl 3-cyclohexene carboxaldehyde kovanol (Takasago) kovyral landolal lanyral Liral lydoucal (A.C.S. International) lyral (IFF) lysinal mugonal lyral

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

	4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde
NIST Chemistry WebBook:	Search Inchi
Canada Domestic Sub. List:	31906-04-4
Pubchem (cid):	91604
Pubchem (sid):	135048904

Publications by PubMed
Baseline series fragrance markers fail to predict contact allergy.
Postnatal odorant exposure induces peripheral olfactory plasticity at the cellular level.
Multicentre patch testing with fragrance mix II and hydroxyisohexyl 3-cyclohexene carboxaldehyde by the Swedish Contact Dermatitis Research Group.
Application of PurpaldÂ® for determination of 3-cyclohexene-1-carboxaldehyde and hydroxyisohexyl 3-cyclohexene carboxaldehyde.
Hydroxyisohexyl 3-cyclohexene carboxaldehyde (lyral) in patch test preparations under varied storage conditions.
Categorization of fragrance contact allergens for prioritization of preventive measures: clinical and experimental data and consideration of structure-activity relationships.
Risk factors associated with sensitization to hydroxyisohexyl 3-cyclohexene carboxaldehyde.
Odorant responsiveness of embryonic mouse olfactory sensory neurons expressing the odorant receptors S1 or MOR23.
Results of patch testing with fragrance mix 1, fragrance mix 2, and their ingredients, and Myroxylon pereirae and colophonium, over a 21-year period.
Two fragrance chemicals may act as toxicants via TRPA1 stimulation rather than via direct mitochondrial action.
Fragrance chemicals lyral and lilial decrease viability of HaCat cells' by increasing free radical production and lowering intracellular ATP level: protection by antioxidants.
Allergic contact dermatitis to fragrances: part 2.
Prevalence of allergic contact dermatitis caused by hydroxyisohexyl 3-cyclohexene carboxaldehyde has not changed in Denmark.
Is hydroxyisohexyl 3-cyclohexene carboxaldehyde sensitization declining in central Europe?
Patch tests with fragrance mix II and its components.
An odor-specific threshold deficit implicates abnormal cAMP signaling in youths at clinical risk for psychosis.
Contact allergy to the 26 specific fragrance ingredients to be declared on cosmetic products in accordance with the EU cosmetics directive.
[Current contact allergens].
Enhanced sensitization and elicitation responses caused by mixtures of common fragrance allergens.
Patch-testing with fragrance mix II.
Can exposure limitations for well-known contact allergens be simplified? An analysis of dose-response patch test data.
Deodorants are the leading cause of allergic contact dermatitis to fragrance ingredients.
Fragrance allergens in 'specific' cosmetic products.
Hydroxyisohexyl 3-cyclohexene carboxaldehyde (LyralÂ®) as allergen: experience from a contact dermatitis unit.
Fragrance mix II in the baseline series contributes significantly to detection of fragrance allergy.
Patch testing with fragrance mix II: results of the IVDK 2005-2008.
Olfactory sensitivity for sperm-attractant aromatic aldehydes: a comparative study in human subjects and spider monkeys.
Fragrance contact allergy: a 4-year retrospective study.
Fragrance allergy: assessing the safety of washed fabrics.
Determination of suspected allergens in cosmetic products by headspace-programmed temperature vaporization-fast gas chromatography-quadrupole mass spectrometry.
A new IFRA Standard on the fragrance ingredient, hydroxyisohexyl 3-cyclohexene carboxaldehyde.
Fragrance contact allergy in Iran.
Clinical relevance of positive patch test reactions to the 26 EU-labelled fragrances.
The dose-response relationship between the patch test and ROAT and the potential use for regulatory purposes.
Quantitative patch and repeated open application testing in hydroxyisohexyl 3-cyclohexene carboxaldehyde sensitive-patients.
Expression patterns of odorant receptors and response properties of olfactory sensory neurons in aged mice.
Hydroxyisohexyl 3-cyclohexene carboxaldehyde allergy: relationship between patch test and repeated open application test thresholds.
Polyvalent type IV sensitizations to multiple fragrances and a skin protection cream in a metal worker.
[Facial allergic contact dermatitis. Data from the IVDK and review of literature].
An odor-specific threshold deficit implicates abnormal intracellular cyclic AMP signaling in schizophrenia.
Hydroxyisohexyl 3-cyclohexene carboxaldehyde (Lyral) is still a frequent allergen.
Allergic contact dermatitis from lyral in an aerosol deodorant.
Allergic contact dermatitis to a perfume containing lyral.
Contact allergy in patients with rosacea: a clinic-based, prospective epidemiological study.
Frequency of and trends in fragrance allergy over a 15-year period.
Recommendation to include fragrance mix 2 and hydroxyisohexyl 3-cyclohexene carboxaldehyde (Lyral) in the European baseline patch test series.
Fragrance ingredient labelling in products on sale in the U.K.
High-performance liquid chromatographic method for the simultaneous determination of 24 fragrance allergens to study scented products.
Selected important fragrance sensitizers in perfumes--current exposures.
Patch test results with patients' own perfumes, deodorants and shaving lotions: results of the IVDK 1998-2002.
Experimental elicitation with hydroxyisohexyl-3-cyclohexene carboxaldehyde-containing deodorants.
[Sensitization to Lyral].
Delayed-type hypersensitivity to fragrance materials in a select North American population.
Odorant responses of olfactory sensory neurons expressing the odorant receptor MOR23: a patch clamp analysis in gene-targeted mice.
Fragrance contact dermatitis in Korea: a joint study.
Clinical update on contact allergy.
Lyral: a fragrance allergen.
Patch testing with a new fragrance mix - reactivity to the individual constituents and chemical detection in relevant cosmetic products.
Patch testing with a new fragrance mix detects additional patients sensitive to perfumes and missed by the current fragrance mix.
Rosacea and contact allergy to cosmetics and topical medicaments--retrospective analysis of multicentre surveillance data 1995-2002.
Cosmetic allergy: incidence, diagnosis, and management.
[Allergy to cosmetics. I. Fragrances].
Functional characterization of a mouse testicular olfactory receptor and its role in chemosensing and in regulation of sperm motility.
The fragrance hand immersion study - an experimental model simulating real-life exposure for allergic contact dermatitis on the hands.
Fragrance allergy in patients with hand eczema - a clinical study.
Hydroxyisohexyl 3-cyclohexene carboxaldehyde- known as Lyral: quantitative aspects and risk assessment of an important fragrance allergen.
[Epidemiologic surveillance of contact allergens. The "monitoring series" of IVDK (Information Network ofDermatologic Clinics for Detection and Scientific Evaluation of Contact Allergy].
Cross-adaptation between olfactory responses induced by two subgroups of odorant molecules.
Hydroxymethyl pentylcyclohexene- carboxaldehyde (Lyral) as a fragrance allergen in the UK.
Principles and methodology for identification of fragrance allergens in consumer products.
Further important sensitizers in patients sensitive to fragrances.
Lyral has been included in the patch test standard series in Germany.
Blocking adenylyl cyclase inhibits olfactory generator currents induced by "IP(3)-odors".
Regulation of cutaneous allergic reaction by odorant inhalation.
Lyral is an important sensitizer in patients sensitive to fragrances.
Allergic contact dermatitis from the fragrance ingredient Lyral in underarm deodorant.
Odorants selectively activate distinct G protein subtypes in olfactory cilia.
Towards structural models of molecular recognition in olfactory receptors.
Existence of multiple receptors in single neurons: responses of single bullfrog olfactory neurons to many cAMP-dependent and independent odorants.
Patch testing with fragrances: results of a multicenter study of the European Environmental and Contact Dermatitis Research Group with 48 frequently used constituents of perfumes.
Chemosensitivity of the osphradium of the pond snail Lymnaea stagnalis
Allergic contact dermatitis from the synthetic fragrances Lyral and acetyl cedrene in separate underarm deodorant preparations.
Molecular modeling of ligand-receptor interactions in the OR5 olfactory receptor.
A quantitative in vitro assay for the evaluation of phototoxic potential of topically applied materials.

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
CHEMBL:	View
HMDB (The Human Metabolome Database):	Search
Export Tariff Code:	2912.30.0000
Typical G.C.
ChemSpider:	View
Wikipedia:	View

Suppliers

Associate Allied Chemicals	Augustus Oils
Azelis UK	Berjé
BOC Sciences	Ernesto Ventós
Fine Fragrances Pvt Ltd	Foreverest Resources
Global Essence	IFF
Indenta Group	Indukern F&F
Jiangyin Healthway	Keva
Kun Shan P&A	Lluch Essence
M&U International	Moellhausen
O'Laughlin Industries	OQEMA
PCW France	Pell Wall Perfumes
Penta International	PerfumersWorld
Perfumery Laboratory	Phoenix Aromas & Essential Oils
Reincke & Fichtner	Santa Cruz Biotechnology
Sigma-Aldrich	SRS Aromatics
Taytonn ASCC	The Good Scents Company
The John D. Walsh Company	The Lermond Company
The Perfumers Apprentice	Augustus Oils Ltd
Azelis UK Ltd.	Berje Inc.
Foreverest Resources Ltd.	Global Essence Inc.
Indukern, S.A. F&F Ingredients Division	Jiangyin Healthway International Trade Co., Ltd
Lluch Essence S.L.	M&U International LLC
Moellhausen S.P.A.	O'Laughlin Industries Inc.
Penta International Corporation	PerfumersWorld Ltd.
SRS Aromatics Ltd	Taytonn ASCC Pte Ltd
The John D. Walsh Company, Inc	Ernesto Ventós S.A.

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	210.31674194336
Specific gravity	@ 25 °C
Pounds per Gallon	8.229 to 8.296
Refractive Index	1.486 to 1.493 @ 20 °C
Acid Value	5 max KOH/g
Vapor Pressure	2.9E-5 mmHg @ 25 °C
Flash Point TCC Value	93.33 °C TCC
logP (o/w)	2.08
Shelf life	24 months (or longer if stored properly.)
Storage notes	Store in cool, dry place in tightly sealed containers, protected from heat and light.
Solubility
alcohol	Yes
water, very slightly	Yes
water, 184.6 mg/L @ 25 °C (est)	Yes
paraffin oil	No
water	No
Stability
alcoholic fine fragrance	Good
antiperspirant	Good
fabric softener	Good
soap	Good
alcoholic lotion	Unspecified
deo stick	Unspecified
detergent perborate	Unspecified
hard surface cleaner	Unspecified
liquid detergent	Unspecified
shampoo	Unspecified

Organoleptic Properties

Odor Type: Floral
floral, muguet, cyclamen, rhubarb, woody
Odor strength	medium
Substantivity	400 hour(s) at 100.00 %
Luebke, William tgsc, (1986)	At 100.00 %. floral muguet cyclamen rhubarb woody
Extraordinary tenacity and diffusivity. A powerful blending agent giving richness throughout all dryout phases of a perfume composition.	Soft delicate floral, lily, cyclamen, lilac note reminiscent of hydrocycitronellal
Used in floral fragrances, mainly muguet accords. Unique as a fine light flower tone that is extremely long lasting.	Sweet and floral
General comment	FLORAL, ALDEHYDIC, SWEET, LILAC
Blends-well-with - Resinoids Styrax	Soft delicate floral lily cyclamen note hydroxycitronellal delicately sweet-light-floral
Arctander writes very enthusiastically about this material: “Lyral was at first believed to be of fixative value only, e. g. in high-class soap perfumes, etc. But it was soon discovered that Lyral has a floral volume which, when properly cultivated’ by the creative perfumer, often outperforms Hydrocitronellal and any other floral chemical or combination of chemicals, its application is therefore continuously expanding from the single floral Muguet to become the must’ in cosmetic fragrances where tenacity and sweet-powdery, stable terminal notes are called for. It blends excellently with the Ionones and with the conventional resinoids (Styrax, Tolu, Peru, etc. ) and it may either accompany Hydroxycitronellal or substitute it.	Floral-muguet, aldehydic, powdery

Occurrences

Potential Uses

Applications	fragrance agents
Odor purposes	Acacia, Agrumen aldehyde, Aldehydic, Almond, Almond blossom, Alpine bouquet, Amber, Ambergris, Ambrette oil replacer, Angel essence, Angelica, Animal, Apple, Apple blossom, Crabapple, Apple green apple, Apple red apple, Ash mountain ash berry, Balsam, Banana, Bark, Bay rum, Bayberry, Bergamot, Blackberry, Blueberry, Bois de rose, Botanical, Bouquet, Boxwood blossom, Boysenberry, Bramble arctic bramble blackberry, Bubble gum, Butterscotch, Calamus oil replacer, Carnation, Cassia blossom, Cedar, Cedar forest, Cherry, Cherry blossom, Chypre, Citrus, Civet, Clematis, Clean linen, Clove blossom, Clover, Colonia, Costus, Country meadow, Crabapple blossom, Cranberry, Cucumber, Curacao, Currant, Cyclamen, Daffodil, Dillenia, Eglantine, Elder berry, Elder flower, Fagonia, Fern, Fetes, Fig, Fir balsam, Fir needle oil replacer, Floral, Florida breeze, Foliage, Forest, Frangipani plumeria, Freesia, Fresh outdoors, Galbanum, Gardenia, Genet, Geranium, Ginger, Ginger white ginger, Gingergrass, Gooseberry, Grape, Grapefruit, Greenhouse, Guaiacwood, Guava, Heather, Herbal, Hibiscus, Hollyberry, Honeysuckle, Huckleberry, Hyacinth, Hydrangea, Iris blossom, Ivy, Jasmin, Jonquil, Juniper berry, Kewda, Kiwi, Kiwi blossom, Kumquat, Lavandin, Lavender, Leather, Lemon, Lemongrass, Lilac, Lily, Lily of the valley, Lime, Linaloe wood, Linden flower, Loganberry, Lotus, Lychee, Magnolia, Mango, Mango flower, Melon, Millefleurs, Mimosa, Mint, Mulberry, Musk, Narcissus, Neroli, New car, Ocean sea, Orange, Orange blossom, Orchid, Pansy, Papaya, Passion blossom, Passion fruit, Peach, Peach blossom, Pear, Pear blossom, Peony, Floral, Petitgrain bergamot petitgrain, Petitgrain lime petitgrain, Petunia, Phlox, Pina colada, Pineapple, Plum, Plum blossom, Plum blossom, Pomegranate, Poppy, Potpourri, Privet, Privet blossom, Quince, Raspberry, Rhubarb, Rose, Rose tea rose, Rose white rose, Saffron, Sandalwood, Scented stock, Spice, Strawberry, Sweet pea, Tangerine, Toffee, Tuberose, Tulip, Vanilla, Violet, Violet leaf, Wallflower, Wintergreen, Wisteria, Woody, Yew, Ylang ylang
Flavoring purposes	Angelica, Caramel, Cloudberry bakeapple, Guaiacwood, Jackfruit, Linaloe wood, Pear prickly pear, Petitgrain bergamot petitgrain, Petitgrain lime petitgrain, Praline, Starfruit, Tea, Tropical
Other purposes	Fantasy blends, Fidji, Joop, Pert plus, Rose wild rose, Tide
Cosmetic purposes	Fragrance, Perfuming agents

Safety Information

Safety information

European information :
Most important hazard(s):
Xi - Irritant
R 43 - May cause sensitisation by skin contact. S 02 - Keep out of the reach of children. S 36 - Wear suitable protective clothing.

Hazards identification

Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
Acute toxicity, Oral (Category 4), H302
GHS Label elements, including precautionary statements

Pictogram

Signal word	Warning
Hazard statement(s)
H302 - Harmful if swallowed H316 - Causes mild skin irritation H320 - Causes eye irritation
Precautionary statement(s)
P264 - Wash skin thouroughly after handling. P270 - Do not eat, drink or smoke when using this product. P301 + P312 - IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P330 - Rinse mouth. P501 - Dispose of contents/ container to an approved waste disposal plant.
Oral/Parenteral Toxicity:
oral-rat LD50 3250 ul/kg BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE BEHAVIORAL: TREMOR National Technical Information Service. Vol. OTS0535072
Dermal Toxicity:
skin-rabbit LD50 11300 ul/kg BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS National Technical Information Service. Vol. OTS0535072
Inhalation Toxicity:
Not determined

Safety in use information

Category:
fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
IFRA Critical Effect:
Dermal sensitization and systemic toxicity
	View the IFRA Standard
View IFRA Standards Library for complete information.
Please review Amendment 49 IFRA documentation for complete information.
IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%):
Category 1: Products applied to the lips
0.02 %
Category 2: Products applied to the axillae
0.02 %
Category 3: Products applied to the face/body using fingertips
0.10 %
Category 4: Products related to fine fragrance
0.20 %
	Category 5: Products applied to the face and body using the hands (palms), primarily leave-on
Category 5A: Body lotion products applied to the body using the hands (palms), primarily leave-on
0.20 %
Category 5B: Face moisturizer products applied to the face using the hands (palms), primarily leave-on
0.20 %
Category 5C: Hand cream products applied to the hands using the hands (palms), primarily leave-on
0.20 %
Category 5D: Baby Creams, baby Oils and baby talc
0.067 %
Category 6: Products with oral and lip exposure
0.20 %
	Category 7: Products applied to the hair with some hand contact
Category 7A: Rinse-off products applied to the hair with some hand contact
0.02 %
Category 7B: Leave-on products applied to the hair with some hand contact
0.02 %
Category 8: Products with significant anogenital exposure
0.067 %
Category 9: Products with body and hand exposure, primarily rinse off
0.20 %
	Category 10: Household care products with mostly hand contact
Category 10A: Household care excluding aerosol products (excluding aerosol/spray products)
0.20 %
Category 10B: Household aerosol/spray products
0.20 %
	Category 11: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate
Category 11A: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
0.067 %
Category 11B: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
0.067 %
Category 12: Products not intended for direct skin contact, minimal or insignificant transfer to skin
91.00 %
	Notes:
IFRA FLAVOR REQUIREMENTS:
Due to the possible ingestion of small amounts of fragrance ingredients from their use in products in Categories 1 and 6, materials must not only comply with IFRA Standards but must also be recognized as safe as a flavoring ingredient as defined by the IOFI Code of Practice (www.iofi.org). For more details see chapter 1 of the Guidance for the use of IFRA Standards.

Recommendation for leerall flavor usage levels up to:
	not for flavor use.