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alpha-Terpineol

CAS No.
98-55-5
Chemical Name:
alpha-Terpineol
Synonyms
Α-TERPINEOL;A-TERPINEOL;l-α-Terpineol;P-MENTH-1-EN-8-OL;2-(4-Methylcyclohex-3-en-1-yl)propan-2-ol;α-Terpineo;Terpenol;TERPINENOL;à-terpineol;TERPINEOL 101 (ALPHA)
CBNumber:
CB6229317
Molecular Formula:
C10H18O
Molecular Weight:
154.25
MDL Number:
MFCD00001557
MOL File:
98-55-5.mol
MSDS File:
SDS
Last updated:2024-04-24 17:21:45

alpha-Terpineol Properties

Melting point 31-35 °C (lit.)
Boiling point 217-218 °C (lit.)
Density 0.93 g/mL at 25 °C (lit.)
vapor pressure 6.48Pa at 23℃
FEMA 3045 | ALPHA-TERPINEOL
refractive index 1.482-1.485
Flash point 90 °C
storage temp. 2-8°C
solubility 0.71g/l
form Liquid After Melting
pka 15.09±0.29(Predicted)
Specific Gravity 0.9386
color Clear colorless
Odor at 100.00 %. pine terpene lilac citrus woody floral
Odor Type terpenic
Water Solubility negligible
JECFA Number 366
Merck 14,9171
BRN 2325137
Dielectric constant 2.8(20℃)
InChIKey WUOACPNHFRMFPN-UHFFFAOYSA-N
LogP 2.6 at 30℃
CAS DataBase Reference 98-55-5(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS) ALPHA-TERPINEOL
FDA UNII 21334LVV8W
NIST Chemistry Reference 3-Cyclohexene-1-methanol, «alpha»,«alpha»4-trimethyl-(98-55-5)
EPA Substance Registry System .alpha.-Terpineol (98-55-5)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319
Precautionary statements  P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
Hazard Codes  Xi
Risk Statements  10-38-36/37/38
Safety Statements  16-37-26-37/39
WGK Germany  1
RTECS  WZ6700000
TSCA  Yes
HS Code  29061400
NFPA 704
2
2 0

alpha-Terpineol price More Price(32)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich CRM40428 alpha-Terpineol solution certified reference material, 2000?μg/mL in methanol, ampule of 1?mL 98-55-5 1mL $124 2024-03-01 Buy
Sigma-Aldrich 04899 α-Terpineol analytical standard 98-55-5 250mg $104 2024-03-01 Buy
Sigma-Aldrich 03420590 α-Terpineol primary reference standard 98-55-5 100mg $304 2023-06-20 Buy
TCI Chemical T0022 α-Terpineol >80.0%(GC) 98-55-5 25mL $21 2024-03-01 Buy
TCI Chemical T0022 α-Terpineol >80.0%(GC) 98-55-5 500mL $121 2024-03-01 Buy
Product number Packaging Price Buy
CRM40428 1mL $124 Buy
04899 250mg $104 Buy
03420590 100mg $304 Buy
T0022 25mL $21 Buy
T0022 500mL $121 Buy

alpha-Terpineol Chemical Properties,Uses,Production

Description

(-)-alpha terpineol is the alpha form of terpineol, a naturally monoterpene alcohol that can be isolated from various kinds of sources such as cajuput oil, pine oil, and petitgrain oil. The alpha form is the major constituent of terpineol. It is a common component in perfumes, cosmetic and flavors. It is also a kind of solvent used for extracting natural spices and as a kind of solvent of acetate fibers. Moreover, it exhibited strong and broad antimicrobial activity against fungi, bacteria and virus. Study has demonstrated that is antibacterial (bactericidal) effect originated from its destroying effect on the cell wall and cell membrane of bacteria. It also has certain anticonvulsant activity.

References

de Sousa, Damiao Pergentino, Lucindo Quintans Jr, and Reinaldo Nóbrega de Almeida. "Evolution of the anticonvulsant activity of α-terpineol."Pharmaceutical Biology 45.1 (2007): 69-70.
Park, Soon-Nang, et al. "Antimicrobial effect of linalool and α- terpineol against periodontopathic and cariogenic bacteria." Anaerobe 18.3 (2012): 369-372.
Dabbah, Roger, V. M. Edwards, and W. A. Moats. "Antimicrobial action of some citrus fruit oils on selected food-borne bacteria." Applied microbiology19.1 (1970): 27-31.

Chemical Properties

α-Terpineol has a characteristic lilac odor with a sweet taste reminiscent of peach on dilution.

Chemical Properties

α-Terpineol is a colorless, crystalline solid, smelling of lilac. The most important commercial grade of terpineol consists of a liquid mixture of isomers that contains mainly α-terpineol and a considerable amount of ?γ-terpineol. This mixture has a stronger lilac odor than does pure crystalline α-terpineol.
Hydrogenation of α-terpineol yields p-menthan-8-ol. Terpineol is readily dehydrated by acids, yielding a mixture of unsaturated cyclic terpene hydrocarbons. Under mildly acidic conditions, terpin hydrate is formed. The most important reaction for the fragrance industry is esterification, particularly acetylation to terpinyl acetate.
Terpineol with its typical lilac odor is one of the most frequently used fragrance substances. It is stable and inexpensive and is used in soaps and cosmetics.

Chemical Properties

Clear colorless liquid after melting

Occurrence

Reported found in more than 150 derivatives from leaves, herbs and flowers; the d-, l- and dl-isomers are known: the d-form is found in the essential oils from Cupressaceae in general; also in the oils of Elettaria cardamomum, star anise, marjoram, clary sage, neroli and others. The l-form is found in Satureia montana, lavandin, cajeput, lime, lemon, cinnamon leaves and the distillates from Pinaceae (with exception of Pinus silvestris, which contains d-terpineol together with racemic form); likewise, Nectandra elaiophora (wood) and petitgrain bigarade. The racemic form is found in cajenne linalool, Thymus caespititius, cajeput, Eucalyptus globulus; mixed with the l-form it is found in petitgrain; a nondefined form of terpineol has been reported in the bitter orange. Reported found in over 260 natural sources including apple, apple juice, apricot, sweet and sour cherry, citrus peel oils and juices, orange, lemon, lime, grapefruit, tangerine, mandarin peels oils and juices, bergamot, cranberry, blueberry, black currant, raspberry, strawberry, guava, grapes, raisin, melon, papaya, peach, pear, pineapple, carrot, celery, peas, potato, bell pepper, tomato, anise, cinnamon, clove, cumin seed, ginger, Mentha oils, pepper, mace, parsley, nutmeg, thyme, Gruyere cheese, parmesan cheese, butter, cooked chicken and beef, hop oil, beer, cognac, rum, wines, tea, nuts, honey, avocado, passion fruit, prune, plums, beans, mushroom, sweet and wild marjoram, starfruit, mango, tamarind, parsnip root, cardamom, coriander seed, rice, quince, litchi, calamus, dill, licorice, lovage root, juniper berry, corn oil, laurel, sweet and bitter fennel, wort, elderberry, loquat, myrtle berry, rosemary, buchu oil, Bourbon vanilla, mountain papaya, turmeric, clary sage, lemon balm, nectarines, naranjilla fruit, cape gooseberry and sea buckthorn.

Uses

A naturally-occuring monoterpene alcohol.Alpha-terpineol is used as an antioxidant, antiseptic, antihypernociception and anti-inflammatory. It is also used as a solvent. It is an important ingredient of pine oil disinfectants. Further, it is used as a fragrance in perfumes, fat denaturant for soap production and synthetic flavoring agent.

Uses

Shows antioxidant effects. Antiseptic. is present in many extracted oils of various plant species, acts as an antihypernociception and anti-inflammatory.

Preparation

Although α-terpineol occurs in many essential oils, only small quantities are isolated, for example, by fractional distillation of pine oils.
A common industrial method of α-terpineol synthesis consists of the hydration of α-pinene or turpentine oil with aqueous mineral acids to give crystalline cis-terpin hydrate (mp 117 °C), followed by partial dehydration to α-terpineol. Suitable catalysts are weak acids or acid-activated silica gel.
Selective conversion of pinene, 3-carene, and limonene or dipentene to terpineol, without terpin hydrate formation is also used. Addition of organic acids (weak acids require catalytic amounts of mineral acids) produces terpinyl esters, which are subsequently hydrolyzed to terpineol, sometimes in situ.

Definition

ChEBI: A terpineol that is propan-2-ol substituted by a 4-methylcyclohex-3-en-1-yl group at position 2.

Aroma threshold values

Detection: 280 to 350 ppb. Aroma characteristics in 1% ethanol: pine-like, woody and resinous with a slight cooling lemon and lime citrus nuance, and a floral dry out.

Taste threshold values

Taste characteristics at 2 to 25 ppm: woody, terpy, lemon and lemon–lime-like with a slight herbal and floral nuance. Taste characteristics at 10 to 25 ppm: citrus woody with a lemon and lime nuance. It has a slight soapy mouthfeel.

General Description

α-Terpineol is a monoterpene alcohol. It is one of the components responsible for the antifungal activity of Melaleuca alternifolia (tea tree) essential oil. The reaction rate constant of α-terpineol with OH radical and ozone was found to be (1.9±0.5)×10-10cm3 molecule-1s-1 and (3.0±0.2)×10-16cm3 molecule-1s-1, respectively.

Flammability and Explosibility

Non flammable

Synthesis

Obtained from terpin hydrate by splitting off water; from pentane tricarboxylic acid by cyclization, followed by esterification to the hydroxy ester, then the unsaturated ester and Grignard to terpineol; also from isoprene and methyl vinyl ketone, using methyl magnesium iodide.

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View Lastest Price from alpha-Terpineol manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
alpha-Terpineol pictures 2024-04-24 alpha-Terpineol
98-55-5
US $8.00-2.00 / kg 1kg 99% g-kg-tons, free sample is available Henan Fengda Chemical Co., Ltd
alpha-Terpineol pictures 2024-04-24 alpha-Terpineol
98-55-5
US $10.00 / kg 1kg 99.6% 100000 Ouhuang Engineering Materials (Hubei) Co., Ltd
alpha-Terpineol pictures 2023-09-06 alpha-Terpineol
98-55-5
US $0.00 / KG 1KG 99% 500000kg Hebei Guanlang Biotechnology Co., Ltd.
  • alpha-Terpineol pictures
  • alpha-Terpineol
    98-55-5
  • US $10.00 / kg
  • 99.6%
  • Ouhuang Engineering Materials (Hubei) Co., Ltd
  • alpha-Terpineol pictures
  • alpha-Terpineol
    98-55-5
  • US $0.00 / KG
  • 99%
  • Hebei Guanlang Biotechnology Co., Ltd.
4-trimethyl-3-cyclohexen-1-methanol (=alpha Terpineol) alpha-Terpineol,97% alpha-Terpineol,95%min α-terpineol,p-menth-1-en-8-ol à,à,4-trimethyl-3-cyclohexene-1-methanol ALPHA-TERPINEOL,PRACTICAL 2-[(1R)-4-methyl-1-cyclohex-3-enyl]propan-2-ol TERPINEOL REIN TERPINEOL 318 TYPE (TERPINEOL N) TERPINEOL, NATURAL Alpha-terpineol, 97%, mixture of alpha- and gamma-terpineol Alpha-terpineol, 98%, mixture of isomers d-1-p-Menthen-8-ol 1-Methyl-4-isopropyl-1-cyclohexen-8-ol 2-(4-Methyl-3-cyclohexenyl)-2-propanol ɑ-Terpineol, 95% min Terpineol schlechthin terpineolschlechthin 2-(4-METHYLCYCLO-3-HEXENYL)-2-PROPANOL 2-(4-METHYL-CYCLOHEX-3-ENYL)-PROPAN-2-OL 1-P-MENTHEN-8-OL 1-P-METHEN-8-OL AURORA KA-475 FEMA 3045 TERPINEOL 350 p-Menth-1-en-8-ol~alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanol 1-methyl-4-isopropyl-1-cyclohexene-8-ol 1-alpha-terpineol TILIANOL SUPER (ALPHA TERPINEOL CRYSTALS) TILIANOL NP TERPINEOL SUPER TERPINEOL PQA pc593 Lily of valley, artificial femanumber3045 dl-alpha-terpineol alpha-Terpinol alpha-terpineole alpha-terpineol,mixtureofisomers alpha-terpinenol alpha,alpha,4-trimethyl-3-cyclohexene-1-methano 2-(4-methylcyclohex-3-enyl)propan-2-ol (alpha-terpineol) 2-(4-Methylcyclohex-3-en-1-yl) α-Terpineol ɑ-Terpineol min alpha-Terpineol 90%, technical grade alpha-Terpineol, 97+% 25GR TERPINEOL, a-(P) α,α,4-Trimethyl-3-cyclohexene-1-methanol 4-(1-Hydroxy-1-methylethyl)-1-methyl-1-cyclohexene TERPINEOL-ALPHA TERPINEOL N TERPINEOL PFG TERPINEOL 200 (ALPHA) ALPHA-TERPINEOL ALPHA, ALPHA, 4-TRIMETHYL-3-CYCLOHEXENE-1-METHANOL 3-CYCLOHEXENE-1-METHANOL, ALPHA, ALPHA, 4-TRIMETHYL TILIANOL NP(TM)