Linalool | dl-Linalool | Alkenyls

Linalool, a natural product isolated and purified from the leaves of Cinnamomum camphora, has been shown to have antinociceptive, antimicrobial, and anti-inflammatory properties.

Synonyms: dl-Linalool; Phantol; AI3-00942

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Quality Control of Linalool Purity: 97% SDS Specification

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NMR

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Product Citations

Is Linalyl Anthranilate Indeed Found In Plant Samples? GC-MS Misidentifications in the Scientific Literature

Pokajewicz, Katarzyna ; Biernat, Tomasz ; Wieczorek, Piotr P ;

DOI: 10.1021/acs.jnatprod.4c01118 PubMed ID: 39682071 J. Nat. Prod.,2024,87(12):2839-2846.

Abstract: Linalyl anthranilate (LNA) has been identified in a number of plant extracts and essential oils by various authors using gas chromatography−mass spectrometry (GC-MS). However, the reported retention behavior of LNA in these studies is inconsistent with the retention data provided in the NIST database. Therefore, the objective of this study was to determine whether the reports of LNA were the result of misidentifications in GC-MS analyses or if the linear NIST retention index was inaccurate. To accomplish this, linalyl anthranilate was synthesized in a two-step procedure, and the resulting product was authenticated using nuclear magnetic resonance (NMR) and GC-MS analyses. This is a new synthetic route to linalyl anthranilate. Subsequently, retention indices for linalyl anthranilate were determined on three commonly used GC phases: polydimethylsiloxane, 5% diphenyl−95% polydimethylsiloxane, and polyethylene glycol. The study confirmed the accuracy of the NIST retention data, establishing the linear retention index data for LNA on a semi-nonpolar GC column as 2051. However, LNA reported in the literature by various authors exhibited a retention index in the elution window of approximately 1000−1400, strongly suggesting that these reports were the result of GC-MS misidentifications. A review of all reported occurrences of LNA in natural samples found no credible evidence of its presence. In many cases, it appears to be a misidentification of linalyl acetate caused by the occurrence of an erroneous spectrum in the older versions of the NIST mass spectra database.

Purchased from AmBeed: 78-70-6

Product Details of Linalool

CAS No. :	78-70-6
Formula :	C₁₀H₁₈O
M.W :	154.25
SMILES Code :	CC(C)=CCCC(C)(O)C=C
Synonyms :	dl-Linalool; Phantol; AI3-00942
MDL No. :	MFCD00008906
InChI Key :	CDOSHBSSFJOMGT-UHFFFAOYSA-N
Pubchem ID :	6549

Safety of Linalool

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H227-H303-H315-H317-H319-H402
Precautionary Statements:	P210-P261-P264-P272-P273-P280-P302+P352-P305+P351+P338-P312-P333+P313-P337+P313-P370+P378-P403+P235-P501

Application In Synthesis of Linalool

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 78-70-6 ]

[ 78-70-6 ] Synthesis Path-Downstream 1~35

1
[ 78-70-6 ]
[ 2051-30-1 ]
[ 78-69-3 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1908,vol. 27,p. 415.
[2]Recueil des Travaux Chimiques des Pays-Bas,1908,vol. 27,p. 415.

2
[ 78-70-6 ]
[ 78-69-3 ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 4725 - 4727.
[2]Journal of the American Chemical Society,2014,vol. 136,p. 13178 - 13181.
[3]RSC Advances,2015,vol. 5,p. 740 - 745.
[4]Tetrahedron,2009,vol. 65,p. 10637 - 10643.
[5]Chemische Berichte,1923,vol. 56,p. 1651.
[6]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1914,vol. 158,p. 1556.
Annales de Chimie (Cachan, France),1914,vol. <9>2,p. 396.
[7]Pharmaceutical Chemistry Journal,1994,vol. 28,p. 65 - 69.
Khimiko-Farmatsevticheskii Zhurnal,1994,vol. 28,p. 46 - 49.
[8]Tetrahedron,1973,vol. 29,p. 1119 - 1125.
[9]Journal of Organic Chemistry,2008,vol. 73,p. 9482 - 9485.
[10]Journal of Molecular Liquids,2020,vol. 298.

3
[ 78-70-6 ]
[ 5205-07-2 ]
[ 98-55-5 ]
[ 107697-32-5 ]
[ 107697-30-3 ]
[ 77967-64-7 ]

References: [1]Tetrahedron,1986,vol. 42,p. 2485 - 2490.

4
[ 78-70-6 ]
[ 106-25-2 ]
[ 106-24-1 ]
[ 98-55-5 ]

References: [1]Tetrahedron Letters,1983,vol. 24,p. 3741 - 3744.
[2]Journal of Organic Chemistry,1986,vol. 51,p. 1310 - 1316.

5
[ 106-25-2 ]
[ 78-70-6 ]
[ 106-24-1 ]
[ 98-55-5 ]

References: [1]Bulletin of the Chemical Society of Japan,1985,vol. 58,p. 844 - 849.
[2]Tetrahedron Letters,1983,vol. 24,p. 3741 - 3744.
[3]Tetrahedron Letters,1983,vol. 24,p. 3741 - 3744.

6
[ 106-25-2 ]
[ 78-70-6 ]
[ 98-55-5 ]

References: [1]Journal of Organic Chemistry,1986,vol. 51,p. 1310 - 1316.

7
[ 106-24-1 ]
[ 78-70-6 ]
[ 106-25-2 ]
[ 98-55-5 ]

References: [1]Bulletin of the Chemical Society of Japan,1985,vol. 58,p. 844 - 849.
[2]Tetrahedron Letters,1983,vol. 24,p. 3741 - 3744.
[3]Tetrahedron Letters,1983,vol. 24,p. 3741 - 3744.

8
[ 115-95-7 ]
[ 78-70-6 ]
[ 106-25-2 ]
[ 106-24-1 ]
[ 141-12-8 ]
[ 105-87-3 ]
[ 98-55-5 ]

References: [1]Journal of Organic Chemistry,1989,vol. 54,p. 1032 - 1036.

9
[ 115-95-7 ]
[ 78-70-6 ]
[ 106-24-1 ]
[ 61434-50-2 ]
[ 98-55-5 ]

References: [1]Tetrahedron Letters,1988,vol. 29,p. 579 - 580.

10
[ 115-95-7 ]
[ 78-70-6 ]
[ 106-24-1 ]
[ 98-55-5 ]

References: [1]Phytochemistry,1990,vol. 29,p. 2143 - 2144.

11
[ 763-10-0 ]
[ 78-70-6 ]
[ 123-35-3 ]
[ 106-25-2 ]
[ 106-24-1 ]
[ 13877-91-3 ]
[ 98-55-5 ]

References: [1]Tetrahedron,1981,vol. 37,p. 2351 - 2358.

12
[ 78130-96-8 ]
[ 78-70-6 ]
[ 106-25-2 ]
[ 106-24-1 ]
[ 98-55-5 ]

References: [1]Journal of the American Chemical Society,1982,vol. 104,p. 1422 - 1424.
[2]Journal of the American Chemical Society,1982,vol. 104,p. 1422 - 1424.
[3]Journal of the American Chemical Society,1982,vol. 104,p. 1422 - 1424.

13
[ 28673-26-9 ]
[ 78-70-6 ]
[ 123-35-3 ]
[ 106-25-2 ]
[ 106-24-1 ]
[ 98-55-5 ]

References: [1]Journal of Organic Chemistry,1986,vol. 51,p. 1310 - 1316.

14
[ 101010-61-1 ]
[ 78-70-6 ]
[ 123-35-3 ]
[ 106-25-2 ]
[ 106-24-1 ]
[ 98-55-5 ]
[ 138-86-3 ]

References: [1]Journal of Organic Chemistry,1986,vol. 51,p. 1310 - 1316.

15
[ 74367-67-2 ]
[ 78-70-6 ]
[ 123-35-3 ]
[ 106-25-2 ]
[ 106-24-1 ]
[ 98-55-5 ]
[ 138-86-3 ]

References: [1]Journal of Organic Chemistry,1986,vol. 51,p. 1310 - 1316.

16
[ 81678-25-3 ]
[ 78-70-6 ]
[ 13877-91-3 ]
[ 98-55-5 ]

References: [1]Heterocycles,1982,vol. 17,p. 125 - 138.

17
[ 104715-14-2 ]
[ 22679-02-3 ]
[ 177698-19-0 ]
[ 78-70-6 ]
[ 80-56-8 ]
[ 106-24-1 ]
[ 98-55-5 ]
[ 138-86-3 ]

References: [1]Journal of the American Chemical Society,1987,vol. 109,p. 5542 - 5544.

18
[ 20321-24-8 ]
[ 78-70-6 ]
[ 106-25-2 ]
[ 106-24-1 ]
[ 98-55-5 ]

References: [1]Tetrahedron,1981,vol. 37,p. 2351 - 2358.

19
[ 22679-02-3 ]
geranyl difluoromethanediphosphonate [ No CAS ]
[ 177698-19-0 ]
[ 78-70-6 ]
[ 80-56-8 ]
[ 106-24-1 ]
[ 98-55-5 ]
[ 138-86-3 ]

References: [1]Journal of the American Chemical Society,1987,vol. 109,p. 5542 - 5544.

20
[ 80359-44-0 ]
[ 78-70-6 ]
[ 106-25-2 ]
[ 106-24-1 ]
[ 98-55-5 ]

21
[ 101010-65-5 ]
[ 78-70-6 ]
[ 98-55-5 ]

References: [1]Journal of Organic Chemistry,1986,vol. 51,p. 1310 - 1316.

22
[ 29171-20-8 ]
[ 78-70-6 ]
[ 78-69-3 ]

References: [1]Pharmaceutical Chemistry Journal,1994,vol. 28,p. 65 - 69.
Khimiko-Farmatsevticheskii Zhurnal,1994,vol. 28,p. 46 - 49.
[2]Pharmaceutical Chemistry Journal,1994,vol. 28,p. 65 - 69.
Khimiko-Farmatsevticheskii Zhurnal,1994,vol. 28,p. 46 - 49.
[3]Russian Journal of Organic Chemistry,2002,vol. 38,p. 150 - 152.

23
[ 78-70-6 ]
[ 106-25-2 ]
[ 106-24-1 ]
[ 98-55-5 ]
[ 586-81-2 ]
[ 138-87-4 ]

References: [1]Journal of the Chemical Society. Chemical communications,1995,p. 1635 - 1636.

24
[ 7664-93-9 ]
[ 64-19-7 ]
[ 78-79-5 ]
[ 78-70-6 ]
[ 106-24-1 ]
[ 98-55-5 ]
[ 6627-74-3 ]

References: [1]Justus Liebigs Annalen der Chemie,1932,vol. 496,p. 55.

25
[ 106-24-1 ]
[ 78-70-6 ]
[ 123-35-3 ]
[ 3779-61-1 ]
[ 98-55-5 ]

References: [1]Journal of Agricultural and Food Chemistry,2000,vol. 48,p. 2033 - 2039.

26
Muscat grape glycosides; mixture of [ No CAS ]
[ 78-70-6 ]
[ 106-22-9 ]
[ 106-25-2 ]
[ 98-55-5 ]

References: [1]Bioscience, Biotechnology and Biochemistry,2000,vol. 64,p. 2179 - 2185.

27
Muscat grape glycosides; mixture of [ No CAS ]
[ 78-70-6 ]
[ 106-22-9 ]
[ 106-24-1 ]
[ 98-55-5 ]

References: [1]Bioscience, Biotechnology and Biochemistry,2000,vol. 64,p. 2179 - 2185.

28
[ 78-70-6 ]
[ 586-62-9 ]
[ 99-87-6 ]
[ 98-55-5 ]
[ 138-86-3 ]

References: [1]Advanced Synthesis and Catalysis,2006,vol. 348,p. 59 - 62.

29
[ 78-70-6 ]
[ 98-55-5 ]

References: [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1991,vol. 40,p. 760 - 762.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1991,p. 862 - 865.

30
[ 78-70-6 ]
[ 78-69-3 ]
[ 2270-57-7 ]

References: [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 1437 - 1442.
[2]Journal of Organic Chemistry,2008,vol. 73,p. 9482 - 9485.

31
[ 763-10-0 ]
[ 78-70-6 ]
[ 123-35-3 ]
[ 106-24-1 ]
[ 586-62-9 ]
[ 98-55-5 ]
[ 2009-00-9 ]
[ 563-34-8 ]
[ 5989-54-8 ]

References: [1]Chemical Communications,2015,vol. 51,p. 3797 - 3800.

32
[ 78-70-6 ]
[ 470-82-6 ]
[ 99-86-5 ]
[ 98-55-5 ]

References: [1]Nature Chemistry,2015,vol. 7,p. 197 - 202.

33
[ 106-24-1 ]
[ 470-82-6 ]
[ 78-70-6 ]
[ 99-86-5 ]
[ 98-55-5 ]

References: [1]Journal of the American Chemical Society,2017,vol. 139,p. 11482 - 11492.

34
[ 78-70-6 ]
[ 470-82-6 ]
[ 586-62-9 ]
[ 99-86-5 ]
[ 98-55-5 ]

References: [1]Journal of the American Chemical Society,2017,vol. 139,p. 11482 - 11492.

35
[ 106-86-5 ]
[ 78-70-6 ]
octakis(dimethylsiloxy)octasilsesquioxane [ No CAS ]
C₈₈H₁₇₆O₂₈Si₁₆ [ No CAS ]

References: [1]Organometallics,2019,vol. 38,p. 3018 - 3024.

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P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
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P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
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P314	Get medical advice/attention if you feel unwell.
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P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
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P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
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P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
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P401
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Physical hazards
Code	Phrase
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H201	Explosive; mass explosion hazard
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
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H316	Causes mild skin irritation
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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

{[proInfo.proName]}

CAS No.: 78-70-6

{[proInfo.proName]}

CAS No.: 78-70-6

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Product Details of Linalool

Safety of Linalool

Application In Synthesis of Linalool

[ 78-70-6 ] Synthesis Path-Downstream 1~35

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