butyl oleate

Butyl oleate is a fatty acid ester commonly used as an emollient and skin conditioning agent in cosmetic and flavor applications.

General Material Description

Butyl oleate is a fatty acid ester composed of butanol and oleic acid, with the molecular formula C₂₂H₄₂O₂. It appears as a clear, oily liquid with a mild fatty odor and flavor profile. Also known by synonyms like butyl (9Z)-9-octadecenoate and 9-octadecenoic acid butyl ester, it is classified chemically as a monoester derived from the unsaturated fatty acid oleic acid. This compound is listed in controlled vocabularies such as CHEBI (ChEBI:82946). Typically derived through esterification of oleic acid with butanol, it may occur naturally in some plant sources like Plumeria rubra. Its mild sensory characteristics make it suitable for use in formulations requiring an emollient with low odor impact.

Occurrence, Applicability & Potential Uses

Butyl oleate occurs naturally in select plant species including Plumeria rubra. It finds wide application as an emollient, providing skin conditioning effects in cosmetic products. Additionally, it serves as a flavoring agent contributing fatty notes in food flavor formulations. The compound is regulated under standards such as REACH (EU), ensuring safe industrial and consumer usage. In cosmetic manufacturing, butyl oleate enhances texture and spreadability of creams and lotions. Its chemical stability and relatively low volatility also permit use in fragrance bases, although recommended usage levels vary depending on regulatory guidelines. These properties support its use in personal care and flavor industries where mild, fatty sensory effects are desired.

Physico-Chemical Properties Summary

Butyl oleate is characterized by a molecular weight of approximately 338.58 g/mol and presents as a clear oily liquid at room temperature. It exhibits a high boiling point between 414 and 415 °C at standard atmospheric pressure, indicating thermal stability suitable for various formulation processes. The compound has a very low vapor pressure at 25 °C (2.0×10⁻⁶ mm Hg), which correlates with low volatility and reduced evaporation losses. Its estimated logP value of 9.75 signifies significant lipophilicity, aligning with its function as a skin-conditioning emollient and solvent in nonpolar media. Butyl oleate is soluble in alcohols but practically insoluble in water, reflecting its hydrophobic nature. The flash point is approximately 93 °C, supporting safe handling under controlled temperatures. Shelf life extends to at least twelve months when stored properly, maintaining consistent physicochemical behavior.

FAQ

What is butyl oleate and what are its main characteristics?

Butyl oleate is a fatty acid ester formed from butanol and oleic acid, possessing the molecular formula C₂₂H₄₂O₂. It is a clear, oily liquid with a mild fatty odor and flavor. Chemically, it functions as an emollient and solvent with high lipophilicity, commonly used in cosmetic and flavor applications. It is known by several synonyms, including butyl (9Z)-9-octadecenoate and oleic acid butyl ester. Due to its physical properties like high boiling point and low vapor pressure, it is stable under typical formulation conditions.

Where does butyl oleate naturally occur and how is it typically used in industry?

Butyl oleate can be found naturally in certain plants such as Plumeria rubra, although industrial supplies are mainly synthesized via esterification of oleic acid with butanol. It is utilized primarily as an emollient and skin conditioning agent in cosmetics, enhancing softness and smoothness of the skin. Additionally, it serves as a fatty flavoring agent in food products. Its chemical stability and low volatility make it useful in fragrance bases and topical formulations. Regulatory standards like REACH (EU) guide its permitted uses and concentrations.

What safety regulations and precautions are associated with butyl oleate?

Butyl oleate is classified under regulatory frameworks such as REACH (EU), which oversee its manufacture and use to ensure consumer safety. According to safety data, it is an irritant to skin and eyes, requiring handling with suitable protective clothing and care to avoid contact. Recommended usage levels exclude fragrance applications in some guidelines. Toxicity data are limited, thus following precautionary measures such as avoiding eye exposure and storing out of reach of children is advised. Safety data sheets and official chemical registries provide detailed handling instructions.

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

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Literature & References

	butyl (Z)-octadec-9-enoate
NIST Chemistry WebBook:	Search Inchi
Canada Domestic Sub. List:	142-77-8
Pubchem (cid):	5354342
Pubchem (sid):	134973407

Publications by Google Patents
Oleic acid ester
Publications by PubMed
In situ alcoholysis of triacylglycerols by application of switchable-polarity solvents. A new derivatization procedure for the gas-chromatographic analysis of vegetable oils.
Lipase immobilized on the hydrophobic polytetrafluoroethene membrane with nonwoven fabric and its application in intensifying synthesis of butyl oleate.
Lipase production in solid-state fermentation monitoring biomass growth of aspergillus niger using digital image processing.
Biodiesel production from triolein and short chain alcohols through biocatalysis.
Esterification of fatty acids using nylon-immobilized lipase in n-hexane: kinetic parameters and chain-length effects.
Biodegradable products by lipase biocatalysis.
Lipid oxidation. Part 2. Oxidation products of olive oil methyl esters.
Lipid oxidation. Part. 1. Effect of free carboxyl group on the decomposition of lipid hydroperoxide.
Spectrophotometric method for estimating enzymatic synthesis of butyl oleate.

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
FDA Indirect Additives used in Food Contact Substances:	View
CHEBI:	View
CHEMBL:	View
HMDB (The Human Metabolome Database):	Search
Export Tariff Code:	2916.15.5000
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Formulations/Preparations: •"kessco" is trademark for a series of fatty acid esters used as plasticizers, softeners, wetting agents, emulsifiers, etc. kessco •"wilmar" is trademark for a series of fatty acids, fatty acid esters & polyesters used in foods, drugs, cosmetics, textiles, polishes, waxes & plastics. wilmar

General Material Information

Preferred name	butyl oleate
Trivial Name	Butyl oleate
Short Description	9-octadecenoic acid (Z)-, butyl ester
Formula	C22 H42 O2
CAS Number	142-77-8
Flavis Number	9.208
ECHA Number	205-559-6
FDA UNII	487I65419Q
Nikkaji Number	J4.353B
Beilstein Number	1728057
MDL	MFCD00053819
COE Number	741
xLogP3-AA	8.80 (est)
Bio Activity Summary	External link
NMR Predictor	External link
Synonyms	advaplast 42 butyl (9Z)-9-octadecenoate butyl (9Z)-octadec-9-enoate butyl (Z)-9-octadecenoate butyl (Z)-octadec-9-enoate butyl cis-9-octadecenoate 1-butyl oleate hallco C 503 kemester 4000 kessco 554 9-octadecenoic acid (9Z)-, butyl ester 9-octadecenoic acid (Z)-, butyl ester (9Z)-9-octadecenoic acid butyl ester (Z)-9-octadecenoic acid butyl ester 9-octadecenoic acid, butyl ester 9-octadecenoic acid, butyl ester, (9Z)- oleic acid butyl ester oleic acid, butyl ester plasthall 503 uniflex BYO vinicizer 30 witcizer 100 9-Octadecenoic acid (9Z)-, butyl ester 9-Octadecenoic acid (Z)-, butyl ester Kesscoflex BO Wilmar Butyl Oleate Witcizer 101 n-Butyl oleate Plasthall 914 Kaolube 804

Suppliers

Acme Synthetic Chemicals	Advanced Biotech
BOC Sciences	Inoue Perfumery
Mohini Organics	Penta International
Santa Cruz Biotechnology	Sigma-Aldrich: Sigma
Stearinerie Dubois	SysKem Chemie
Penta International Corporation

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	338.57513427734
Boiling Point	414 to 415°C @ 760 mm Hg
Vapor Pressure	2.0E-6 mmHg @ 25 °C
Flash Point TCC Value	93.33 °C TCC
logP (o/w)	9.754 est
Shelf life	12 months (or longer if stored properly.)
Solubility
alcohol	Yes
water, 5.717e-005 mg/L @ 25 °C (est)	Yes
water	No

Organoleptic Properties

Odor Type: Fatty
fatty
Odor strength	low
General comment	At 100.00 %. mild fatty
Flavor Type: Fatty
fatty
General comment	Fatty

Occurrences

Potential Uses

Applications	cosmetic and flavor agents
Other purposes	Emollients , Skin conditioning
Cosmetic purposes	Fragrance , Skin conditioning , Skin conditioning - emollient

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/38 - Irritating to skin and eyes. S 02 - Keep out of the reach of children. S 24/25 - Avoid contact with skin and eyes. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 36 - Wear suitable protective clothing.

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