Dipentene
CAS Number: 138-86-3
Molecular Weight: 136.23752000
Molecular Formula: C10H16



APPLICATIONS


Benefits of Dipentene:

A special pleasant aroma
A cyclic Terpene
Disolve anhydrous ethanol, ether, chloroform and other organic solvents and insoluble in water


Dipentene was employed as a solvent in the reaction media for enzymatic synthesis of phosphatidylserine.


Identified uses of Dipentene:

Laboratory chemicals
Manufacture of substances


Dipentene is used as a solvent for resins, alkyds and waxes and to make paints, enamels, lacquers and polishes.
Furthermore, Dipentene is used as a perfumery composition for soaps, personal care products and cosmetics.
Dipentene is used as an intermediate for terpene resins, carvone, terylene, and rubber chemicals. It is used as an oils dispersant, metal dryer.

Dipentene is used as a substitute for chlorinated solvents in degreasing metals for cleaning in the electronic industry.
Moreover, Dipentene is used as starting material for the synthesis of terpene resin.
Dipentene is used as a gallstone solubilizer in pharmaceutical industry.


Applications of Dipentene:

Products used for cleaning or safety in an occupational or industrial setting (e.g. industrial cleaning supplies or laundry detergent, eye wash, spill kits)
Cleaning and household care products that can not be placed in a more refined category
Home air fresheners, including candles with a fragrance
Bathtub, tile, and toilet surface cleaners
Carpet-cleaning products that may be used directly (or require dilution), includes solutions that may be used by hand or in mechanical carpet cleaners
Hard floor cleaners, including pre-moistened wipes
Products that impart a shine to solid floors
Detergent based products used during the hand washing of dishes
Cleaning products for general household cleaning, which do not fit into a more refined category
Products used to control microbial pests on hard surfaces or laundry
Products used to clean glass, mirrors, and windows
Products used to clean hard surfaces in the home, including kitchen specific hard surface cleaners
Heavy duty hard surface cleaning products that may require dilution prior to use (i.e., may be concentrated)
Products used in washing machines to clean fabrics
Products used to clean grills, ovens, or range cooktops
Products applied to footwear to color, polish, clean, or add a protective surface
flavouring
fragrance
Products for removing grease and other hydrophobic materials from hard surfaces
Paint or stain related products that do not fit into a more refined category
Products used on wooden surfaces, including decks, to impart transparent or semitransparent color
Products for coating and protecting household surfaces other than glass, stone, or grout
General personal care products which do not fit into a more refined category
Facial cleansing products (excluding scrubs), for acne treatment
Multicomponent body care or bath set for which individual products are not designated
Products related to body hygiene which do not fit into a more refined category
Bar and other solid soaps
Body cleaners containing abrasives or exfoliants
Body cleaners, washes, shower gels
Antibacterial products for application to hands
Liquid hand soaps
Lipophilic products applied to skin (excluding baby oils)
Personal care products intended for use by children, which do not fit into a more specific category
Toothpastes and dentrifices
Deodorants and antiperspirants
Facial cleansing and moisturizing products which do not fit into a more refined category
Moisturizers, lotions, and creams for treating the face (excluding eye-specific products)
Leave-on masks or peels for treatment of the face
Miscellaneous products for application to feet, including scrubs, lotions, deodorants, and treatments for skin and nail problems
Fragrances, colognes, and perfumes
General moisturizing products which do not fit into a more refined category
Products specifically marketed for application to hands or body to moisturize or improve skin characteristics (excluding baby lotion)
General hair styling or hair care products which do not fit into a more refined category
Products for removing oil and dirt from hair
Rinse-out everyday hair conditioners (excluding combo shampoo/conditioner products)
Leave-in everyday hair conditioners and detanglers
Spray fixatives for hair


Dipentene is used in products for imparting hold, shine, or texture to hair.
Besides, Dipentene is used in shampoos, including dual shampoo/conditioner products.
Dipentene is used in make-up or cosmetic products which do not fit into a more refined category.

Dipentene is used in eye liners or brow coloring products.
In addition, Dipentene is used in foundation make-up and concealers.

Dipentene is used in lip products primarily for protection.
Additionally, Dipentene is used in colored lip products, excluding glosses.

Dipentene is used in adhesives for reparing fingernails or attaching artificial nails.
More to that, Dipentene is used in chemical products for tanning, staining, or coloring the skin.

Dipentene is used in products applied to the skin following shaving to provide scent, or improve skin characteristics.
Further to that, Dipentene is used in cleaning and lubricating products for hair clippers.
Dipentene is used in shaving creams, foams, balms and soaps.

Dipentene is used in solid or powdered products added to bathwater including bath salts, soaks, and fizzes.
Furthermore, Dipentene is used in products added to bath water to create bubbles, may provide cleaning, fragrance, or improve skin characteristics (including bubble bath marketed to babies or children).

Dipentene is used in products applied to the skin to block harmful effects of sunlight.
Moreover, Dipentene is used in products for repelling insects from skin.
Dipentene is used in insecticides, for interior or exterior use.

Dipentene is used in products for masking odors or adding fragrance to car cabin air.
Besides, Dipentene is used in auto body waxes and coatings, excluding combo wash/wax products.

Dipentene is used in flavorings, fragrances, cosmetics and as a solvent and wetting agent.
Also, Dipentene is used to make resins, insecticides, insect repellants, and animal repellants.

Dipentene is used as a dissolving agent for gallstones and gutta-percha.
In addition, Dipentene is used in floor waxes and furniture polishes.
Dipentene occurs naturally in essential oils of many plants and is a minor constituent of turpentine.

Dipentene is monomer in terpene resins; solvent for oleoresinous products; general wetting and dispersing agent; chemical intermediate for various organic compounds; flavor ingredient (orange-like).
One important use for Dipentene is its use as a chiral starting material for the synthesis of (R)-(-)-carvone.

An application for printed circuit board cleaners has also been developed using dipentene and limonene with emulsifying surfactants to facilitate removal by rinsing in water.


Industry Uses of Dipentene:

Adhesion/cohesion promoter
Fragrance
Fuels and fuel additives
Intermediates
Monomers
Odor agents


Consumer Uses:

Fragrance
Fuels and fuel additives
Odor agents


Dipentene is common as a dietary supplement and as a fragrance ingredient for cosmetics products.
As the main fragrance of citrus peels, Dipentene is used in food manufacturing and some medicines, such as a flavoring to mask the bitter taste of alkaloids, and as a fragrance in perfumery, aftershave lotions, bath products, and other personal care products.
Dipentene is also used as a botanical insecticide.

Additionally, Dipentene is used in the organic herbicides.
Dipentene is added to cleaning products, such as hand cleansers to give a lemon or orange fragrance (see orange oil) and for its ability to dissolve oils.
In contrast, Dipentene has a piny, turpentine-like odor.

Dipentene is used as a solvent for cleaning purposes, such as adhesive remover, or the removal of oil from machine parts, as it is produced from a renewable source (citrus essential oil, as a byproduct of orange juice manufacture).
More to that, Dipentene is used as a paint stripper and is also useful as a fragrant alternative to turpentine.

Dipentene is also used as a solvent in some model airplane glues and as a constituent in some paints.
Commercial air fresheners, with air propellants, containing Dipentene are used by stamp collectors to remove self-adhesive postage stamps from envelope paper.

Dipentene is also used as a solvent for fused filament fabrication based 3D printing.
Printers can print the plastic of choice for the model, but erect supports and binders from High Impact Polystyrene (HIPS), a polystyrene plastic that is easily soluble in Dipentene.

In preparing tissues for histology or histopathology, Dipentene is often used as a less toxic substitute for xylene when clearing dehydrated specimens.
Clearing agents are liquids miscible with alcohols (such as ethanol or isopropanol) and with melted paraffin wax, in which specimens are embedded to facilitate cutting of thin sections for microscopy.

Dipentene is also combustible and has been considered as a biofuel.
With its pine, lime like aroma, Dipentene is considered refreshing in flavours and fragrances.
Dipentene delivers herbal, citrus, aromatic, flavours that hold hints of pine, mint, and wood and are often described as being tropical.


Dipentene has excellent perfumery and flavouring properties, and is often used in:

Cosmetics
Soap, a variety of toiletries, and air freshener
Hair colour
Household cleaning products
Nappies
Food flavourant


From an industrial perspective, Dipentene’s effective solvent properties make it ideal for applications in:

Resins, alkyds, enamels, lacquers, paints, and varnish
Rubber processing and reclaiming
Industrial cleaning and deodorising products including waxes and polishes, offering germicidal, fungicidal, and insecticidal properties
Deoderisers, re-odorants, and masking agents
Oil extraction
Degreaser (particularly for metals) and defoamer
Pesticides
Some applications in the pharmaceutical sector



DESCRIPTION


Dipentene (Limonene) is a monoterpene olefin having potential applications in polymer and fuel chemistry.
Further to that, Dipentene is also widely used as flavoring and fragrance agent.
Dipentene (limonene) is a promising green solvent.

Kinetics of the reactions of Dipentene with OH and OD radicals has been investigated in a low pressure flow tube reactor coupled with a quadrupole mass spectrometer.

Dipentene (also called D-Limonene), is a terpene liquid found in various volatile oils such as cardamon, mace, nutmeg , turpentine oil.
Furthermore, Dipentene is mainly composed of Limonene, beta-Phellandrene, Myrcene and other terpenes.

Dipentene is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the oil of citrus fruit peels.
The d-isomer, occurring more commonly in nature as the fragrance of oranges, is a flavoring agent in food manufacturing.
Dipentene is also used in chemical synthesis as a precursor to carvone and as a renewables-based solvent in cleaning products.

The less common l-isomer has a piny, turpentine-like odor, and is found in the edible parts of such plants as caraway, dill, and bergamot orange plants.

Dipentene is a relatively stable monoterpene and can be distilled without decomposition, although at elevated temperatures it cracks to form isoprene.
Moreover, Dipentene oxidizes easily in moist air to produce carveol, carvone, and limonene oxide.
With sulfur, Dipentene undergoes dehydrogenation to p-cymene.

Dipentene occurs commonly as the (R)-enantiomer, but racemizes to dipentene at 300 °C.
When warmed with mineral acid, Dipentene isomerizes to the conjugated diene α-terpinene (which can also easily be converted to p-cymene).
Evidence for this isomerization includes the formation of Diels–Alder adducts between α-terpinene adducts and maleic anhydride.

Dipentene is possible to effect reaction at one of the double bonds selectively.
Anhydrous hydrogen chloride reacts preferentially at the disubstituted alkene, whereas epoxidation with mCPBA occurs at the trisubstituted alkene.
In another synthetic method Markovnikov addition of trifluoroacetic acid followed by hydrolysis of the acetate gives terpineol.



PROPERTIES


Appearance Form: liquid
Odor: No data available
Odor Threshold: No data available
pH: No data available
Melting point/freezing point:
Melting point/range: -89 °C
Initial boiling point and boiling range: 170 - 180 °C - lit.
Flash point: 43 °C - closed cup
Evaporation rate: No data available
Flammability (solid, gas): No data available
Upper/lower flammability or explosive limits:
Upper explosion limit: 6,1 %(V)
Lower explosion limit: 0,7 %(V)
Vapor pressure: 1 hPa at 20 °C
Vapor density: 4,7 - (Air = 1.0)
Density: 0,86 g/mL at 20 °C - lit.
Relative density: No data available
Water solubility at 20 °C: insoluble
Partition coefficient (n-octanol/water): log Pow: 4,57
Autoignition temperature: No data available
Decomposition temperature: No data available
Viscosity:
Viscosity, kinematic: No data available
Viscosity, dynamic: No data available
Explosive properties: No data available
Oxidizing properties: No data available
Molecular Weight: 136.23
XLogP3-AA: 13.4
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 0
Rotatable Bond Count: 1
Exact Mass: 136.125200510
Monoisotopic Mass: 136.125200510
Topological Polar Surface Area: 0 Ų
Heavy Atom Count: 10
Formal Charge: 0
Complexity: 163
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes



FIRST AID


Description of first-aid measures:

General advice:

Consult a physician.
Show this material safety data sheet to the doctor in attendance.


If inhaled:

If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
Consult a physician.


In case of skin contact:

Wash off with soap and plenty of water.
Consult a physician.


In case of eye contact:

Flush eyes with water as a precaution.


If swallowed:

Do NOT induce vomiting.
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Consult a physician.


Most important symptoms and effects, both acute and delayed:

The most important known symptoms and effects are described in the labelling.


Indication of any immediate medical attention and special treatment needed:

No data available



HANDLING AND STORAGE


Precautions for safe handling:

Advice on safe handling:

Avoid contact with skin and eyes.
Avoid inhalation of vapor or mist.


Advice on protection against fire and explosion:

Keep away from sources of ignition - No smoking.
Take measures to prevent the build up of electrostatic charge.


Hygiene measures:

Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.


Conditions for safe storage, including any incompatibilities:

Storage conditions:

Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Store in cool place.


Storage class:

Storage class (TRGS 510): 3: Flammable liquids


Specific end use(s):

Apart from the uses mentioned above, no other specific uses are stipulated.


Storage:

Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Keep container tightly closed in a dry and well-ventilated place.
Store in cool place.



SYNONYMS


DIPENTENE ( D-LIMONENE / CITRUS & PINUS )
1-methyl-4-(1-methylethenyl)cyclohexene
Cajeputene
Cinene
Ciene
p-Menthdecene
limonene
p-mentha-1,8-diene
4-isopropenyl-1-methyl-Cyclohexene
Dipenten
DL-p-mentha-1,8-diene
4-Isopropenycyclohexene; Mentha-1,8-diene
Mentha-1,8-diene, DL
Menthadiene
Methyl-4-(1-methylethenyl)cyclohexene
Methyl-4-isoprocyclohexene
Methyl-4-isopropenylcyclohexene
Monocyclic terpene hydrocarbons
Terpodiene
4-(1-methylethenyl)-1-methylNO:138-86-3
LIMONENE
Dipentene
138-86-3
Cinene
Cajeputene
Kautschin
DL-Limonene
Dipenten
Eulimen
Nesol
p-Mentha-1,8-diene
1,8-p-Menthadiene
Cyclohexene, 1-methyl-4-(1-methylethenyl)-
Cajeputen
Limonen
Cinen
1-Methyl-4-(1-methylethenyl)cyclohexene
Inactive limonene
Acintene DP dipentene
Polylimonene
Dipanol
Unitene
alpha-Limonene
Flavor orange
Orange flavor
Goldflush II
(+/-)-Limonene
Acintene DP
4-Isopropenyl-1-methyl-1-cyclohexene
4-Isopropenyl-1-methylcyclohexene
Di-p-mentha-1,8-diene
1,8(9)-p-Menthadiene
DL-4-Isopropenyl-1-methylcyclohexene
Limonene, dl-
1-methyl-4-prop-1-en-2-ylcyclohexene
p-Mentha-1,8-diene, dl-
1-Methyl-4-isopropenyl-1-cyclohexene
1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
7705-14-8
MENTHA-1,8-DIENE (DL)
Dipentene, technical grade
.alpha.-Limonene
NSC 21446
PC 560
Limonene, (+/-)-
.delta.-1,8-Terpodiene
Terpenes and Terpenoids, limonene fraction
CHEBI:15384
1-Methyl-4-isopropenylcyclohexene
NSC-844
NSC-21446
9MC3I34447
65996-98-7
NCGC00163742-03
Polydipentene
Limonene polymer
DSSTox_CID_9612
d,l-Limonene
Dipentene polymer
DSSTox_RID_78787
DSSTox_GSID_29612
Dipentene 200
(+-)-Dipentene
Orange x
(+-)-Linonene
Caswell No. 526
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (.+/-.)-
delta-1,8-Terpodiene
(+-)-alpha-Limonene
Dipentene, crude
CAS-138-86-3
HSDB 1809
NSC 844
p-Mentha-1,8-diene, (+-)-
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (R)-
EINECS 205-341-0
EINECS 231-732-0
UN2052
1-Methyl-p-isopropenyl-1-cyclohexene
DIPENTENE (+-)
EPA Pesticide Chemical Code 079701
Terpodiene
Ciene
Cyclil decene
AI3-00739
UNII-9MC3I34447
Achilles dipentene
Dipentene, tech.
4-isopropenyl-1-methyl-cyclohexene
Dipentene, technical, for use as solvent (for the paint industry), mixture of various terpenes
c0626
Mentha-1,8-diene
p-Mentha-1, dl-
Dipentene, homopolymer
d(R)-4-Isopropenyl-1-methylcyclohexene
(.+-.)-Limonene
(.+-.)-Dipentene
LIMONENE [HSDB]
LIMONENE [MI]
(.+/-.)-Dipentene
(.+/-.)-Limonene
DIPENTENE 38 PF
DIPENTENE [VANDF]
ESSENCE DE PIN PF
(1)-1-Methyl-4-(1-methylvinyl)cyclohexene
DL-p-mentha-1,8-diene
Mentha-1,8-diene, DL
(+-)-(RS)-limonene
DIPENTEN [WHO-DD]
Cyclohexene, (.+-.)-
Dipentene, p.a., 95%
p-Mentha-1,8(9)-diene
Dipentene, mixture of isomers
CHEMBL15799
Monocyclic terpene hydrocarbons
Methyl-4-isopropenylcyclohexene
NSC844
(.+/-.)-.alpha.-Limonene
DTXSID2029612
(+/-)-p-Mentha-1,8-diene
p-Mentha-1, (.+-.)-
HMS3264E05
Pharmakon1600-00307080
Methyl-4-isopropenyl-1-cyclohexene
HY-N0544
NSC21446
Tox21_112068
Tox21_201818
Tox21_303409
MFCD00062992
NSC757069
STK801934
1-methyl-4-isopropenylcyclohex-1-ene
LIMONENE, (+/-)- [II]
AKOS009031280
Cyclohexene, 4-Isopropenyl-1-methyl-
Methyl-4-(1-methylethenyl)cyclohexene
WLN: L6UTJ A1 DY1 & U1
CCG-214016
p-Mentha-1,8-diene, (.+/-.)-
p-Mentha-1,8-diene, polymers (8CI)
SB44847
UN 2052
(+/-)-p-Mentha-1,8-diene homopolymer
Limonene 1000 microg/mL in Isopropanol
NCGC00163742-01
NCGC00163742-02
NCGC00163742-04
NCGC00163742-05
NCGC00257291-01
NCGC00259367-01
Terpenes andTerpenoids, limonene fraction
8016-20-4
8050-32-6
NCI60_041856
p-Mentha-1,8-diene, homopolymer (7CI)
1-methyl-4-(1-methylethenyl) cylcohexene
1-methyl-4-(prop-1-en-2-yl)cyclohexene
4-(1-methylethenyl)-1-methyl-cyclohexene
Dipentene [UN2052] [Flammable liquid]
Cyclohexene, 1-methyl-4-(1-methylethynyl)
DB-053490
DB-072716
CS-0009072
FT-0600409
FT-0603053
FT-0605227
L0046
EN300-21627
C06078
D00194
E88572
1-METHYL-4-PROP-1-EN-2-YL-CYCLOHEXENE
AB01563249_01
Q278809
SR-01000872759
J-007186
J-520048
SR-01000872759-1
TERPIN MONOHYDRATE IMPURITY C [EP IMPURITY]
(+/-)-1-METHYL-4-(1-METHYLETHENYL)CYCLOHEXENE
4B4F06FC-8293-455D-8FD5-C970CDB001EE
Dipentene, mixt. of limonene, 56-64%, and terpinolene, 20-25%
555-08-8
8022-90-0