Cannabis Compound Database: Showing Compound Card for hexadecanol-1 (CDB000267)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (5)transporters (1) Show 8 proteins XML

Record Information

Version

1.0

Created at

2020-03-19 00:27:52 UTC

Updated at

2020-12-07 19:07:18 UTC

CannabisDB ID

CDB000267

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

hexadecanol-1

Description

Cetyl alcohol, also known as 1-hexadecanol and palmityl alcohol, is a solid organic compound and a member of the alcohol class of compounds. Its chemical formula is CH3(CH2)15OH. At room temperature, Cetyl alcohol takes the form of a waxy white solid or flakes. It belongs to the group of fatty alcohols. With the demise of commercial whaling, cetyl alcohol is no longer primarily produced from whale oil, but instead either as an end-product of the petroleum industry or produced from vegetable oils such as palm oil and coconut oil. Production of cetyl alcohol from palm oil gives rise to one of its alternative names, palmityl alcohol. 1-Hexadecanol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 1-Hexadecanol is one of the simple alcohols found in cannabis (PMID: 6991645 ). It has a waxy or oily aroma and a ‚Äúclean cloth‚Äù waxy or oily taste. It is used in the food and cosmetic industry as an emollient, an emulsifying agent, a foam boosting agent, a masking agent, a surfactant, a viscosity controlling agent and a pacifying agent. Hexadecanol is found in, or is added to, shampoos, conditioners, toothpaste, inks, paints, pharmaceuticals, skin creams and lotions. It is also added to certain hard candies and frozen treats. People who suffer from eczema can be sensitive to hexadecanol as it is sometimes included in medications used for the treatment of eczema (PMID: 15059111 ). Cetyl alcohol is also found in cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1-Cetanol	ChEBI
1-Hexadecyl alcohol	ChEBI
16-Hexadecanol	ChEBI
Cetanol	ChEBI
Cetyl alcohol	ChEBI
Cetylalkohol	ChEBI
Hexadecanol	ChEBI
N-1-Hexadecanol	ChEBI
N-Hexadecyl alcohol	ChEBI
Palmityl alcohol	ChEBI
1-Hexadecyl alc	HMDB
1-Hexanedecanol	HMDB
1-Hydroxyhexadecane	HMDB
Adol	HMDB
Adol 52	HMDB
Adol 52 NF	HMDB
Adol 52nf	HMDB
Adol 54	HMDB
Alcohol C-16	HMDB
Aldol 54	HMDB
Alfol 16	HMDB
Atalco C	HMDB
C16 Alcohol	HMDB
Cachalot C-50	HMDB
Cachalot C-50 NF	HMDB
Cachalot C-51	HMDB
Cachalot C-52	HMDB
Ceraphyl ica	HMDB
Cetaffine	HMDB
Cetal	HMDB
Cetalol ca	HMDB
Cetostearyl alcohol	HMDB
Cetyl alcohol NF	HMDB
Cetylic alcohol	HMDB
Cetylol	HMDB
Crodacol C	HMDB
Crodacol C70	HMDB
Crodacol C95NF	HMDB
Crodacol-cas	HMDB
Crodacol-cat	HMDB
Cyclal cetyl alcohol	HMDB
Dehydag wax 16	HMDB
Dytol F-11	HMDB
Elfacos C	HMDB
Epal 16nf	HMDB
Ethal	HMDB
Ethol	HMDB
Eutanol g16	HMDB
Exxal 16	HMDB
Fancol ca	HMDB
Fatty alcohol	HMDB
Hexadecan-1-ol	HMDB
Hexadecanol NF	HMDB
Hexadecyl alcohol	HMDB
Hyfatol	HMDB
Hyfatol 16	HMDB
Isocetyl alcohol	HMDB
Isohexadecanol	HMDB
Isohexadecyl alcohol	HMDB
Lanette 16	HMDB
Lanol C	HMDB
Lipocol C	HMDB
Lorol 24	HMDB
Lorol C16	HMDB
LorolL 24	HMDB
Loxanol K	HMDB
Loxanol K extra	HMDB
Loxanwachs SK	HMDB
Loxiol VPG 1743	HMDB
Michel xo-150-16	HMDB
Myristyl alcohol	HMDB
N-Cetyl alcohol	HMDB
N-Hexadecan-1-ol	HMDB
N-Hexadecanol	HMDB
Normal primary hexadecyl alcohol	HMDB
Philcohol 1600	HMDB
Product 308	HMDB
Rita ca	HMDB
Siponol CC	HMDB
Siponol wax-a	HMDB
SSD	HMDB
SSD RP	HMDB
Cetyl alcohol, 14C-labeled	HMDB
Cetyl alcohol, aluminum salt	HMDB
1-Hexadecanol	ChEBI

Chemical Formula

C₁₆H₃₄O

Average Molecular Weight

242.44

Monoisotopic Molecular Weight

242.261

IUPAC Name

hexadecan-1-ol

Traditional Name

cetyl alcohol

CAS Registry Number

36311-34-9

SMILES

CCCCCCCCCCCCCCCCO

InChI Identifier

InChI=1S/C16H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h17H,2-16H2,1H3

InChI Key

BXWNKGSJHAJOGX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Long-chain fatty alcohols

Alternative Parents

Substituents

Long chain fatty alcohol
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain primary fatty alcohol (CHEBI:16125 )
fatty alcohol 16:0 (CHEBI:16125 )
Fatty alcohols (C00823 )
Fatty alcohols (LMFA05000061 )
a small molecule (CPD-348 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Plant:

Cucurbitaceae

Biological location:

Biofluid and excreta:

Cell and elements:

Extracellular

Cell:

Fibroblast

Subcellular:

Role

Biological role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	49.3 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.3e-05 mg/mL at 25 °C	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	7.17	ALOGPS
logP	6.14	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	16.84	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	77.35 m³·mol⁻¹	ChemAxon
Polarizability	34.38 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0a5c-9000000000-f3299e52ea0593788e37	2014-09-20	View Spectrum
GC-MS	hexadecanol-1, non-derivatized, GC-MS Spectrum	splash10-0f72-7931000000-00a8faa3fd4f0c38a405	Spectrum
GC-MS	hexadecanol-1, 1 TMS, GC-MS Spectrum	splash10-0f6t-9531000000-0dc2948d10d835886750	Spectrum
GC-MS	hexadecanol-1, non-derivatized, GC-MS Spectrum	splash10-0a4l-9000000000-1be6f87af09f0bc4339f	Spectrum
GC-MS	hexadecanol-1, non-derivatized, GC-MS Spectrum	splash10-0a4l-9000000000-83f0c3f9a7d1a2d70b83	Spectrum
GC-MS	hexadecanol-1, non-derivatized, GC-MS Spectrum	splash10-0a59-9100000000-51d2315e018d6ebbe25d	Spectrum
GC-MS	hexadecanol-1, non-derivatized, GC-MS Spectrum	splash10-0f72-7931000000-00a8faa3fd4f0c38a405	Spectrum
GC-MS	hexadecanol-1, non-derivatized, GC-MS Spectrum	splash10-0f6t-9531000000-0dc2948d10d835886750	Spectrum
GC-MS	hexadecanol-1, non-derivatized, GC-MS Spectrum	splash10-0f72-9821000000-ee82a405e4a854526b64	Spectrum
Predicted GC-MS	hexadecanol-1, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0bvl-7910000000-c4f032970214d082f3cf	Spectrum
Predicted GC-MS	hexadecanol-1, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9640000000-6df3de611756e2218c31	Spectrum
Predicted GC-MS	hexadecanol-1, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0udi-0910000000-b74545433556690d2c46	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0udi-0900000000-7aab213ad736e774476c	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0udi-0900000000-55a8272e13510c85c06a	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0a4l-9000000000-a4776db6cf6d30dfb50e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , Positive	splash10-0a4l-9000000000-83f0c3f9a7d1a2d70b83	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-HX-100) , Positive	splash10-0a59-9100000000-7ca85869bfef10e335f3	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004l-0190000000-b08f970abae4433e0d8b	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004l-5690000000-d0c4cde89f48e5218c95	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9500000000-455427a3ee7620a41403	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0090000000-3fdb1b4b343c7ad295bf	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0090000000-a848ffe1f9f31e21601c	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01vp-9740000000-15fb3da54ceed633096b	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-4190000000-44af6a0edc2288305d9c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0abc-9110000000-a07d84c82c62e530754e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-dc9968082483b614a723	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0090000000-3ce1eb2d48c904ebe347	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0090000000-e0b832e3e0af19f4f9ae	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9880000000-0db321e9b8178e2cdc8f	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Plasmalogen Synthesis		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Alkyldihydroxyacetonephosphate synthase, peroxisomal	AGPS	2q31.2	O00116	details
Fatty acyl-CoA reductase 1	FAR1	11p15.2	Q8WVX9	details
Fatty acyl-CoA reductase 2	FAR2	12p11.22	Q96K12	details
Acyl-CoA wax alcohol acyltransferase 1	AWAT1	Xq13.1	Q58HT5	details
Acyl-CoA wax alcohol acyltransferase 2	AWAT2	Xq13.1	Q6E213	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Platelet glycoprotein 4	CD36	7q11.2	P16671	details

Metal Bindings

Not Available

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Free fatty acid receptor 1	FFAR1	19q13.1	O14842	details
Free fatty acid receptor 4	FFAR4	10q23.33	Q5NUL3	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0003424

DrugBank ID

DB09494

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003051

KNApSAcK ID

Not Available

Chemspider ID

2581

KEGG Compound ID

C00823

BioCyc ID

CPD-348

BiGG ID

Not Available

Wikipedia Link

Cetyl_Alcohol

METLIN ID

6927

PubChem Compound

2682

PDB ID

Not Available

ChEBI ID

16125

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
Soga F, Katoh N, Kishimoto S: Contact dermatitis due to lanoconazole, cetyl alcohol and diethyl sebacate in lanoconazole cream. Contact Dermatitis. 2004 Jan;50(1):49-50. doi: 10.1111/j.0105-1873.2004.00271j.x. [PubMed:15059111 ]

Enzymes

Enzyme Details

1. Alkyldihydroxyacetonephosphate synthase, peroxisomal

General function:: Involved in catalytic activity
Specific function:: 1-acyl-glycerone 3-phosphate + a long-chain alcohol = an alkyl-glycerone 3-phosphate + a long-chain acid anion
Gene Name:: AGPS
Uniprot ID:: O00116
Molecular weight:: 72911.2

Enzyme Details

2. Fatty acyl-CoA reductase 1

General function:: Involved in catalytic activity
Specific function:: Catalyzes the reduction of saturated fatty acyl-CoA with chain length C16 or C18 to fatty alcohols.
Gene Name:: FAR1
Uniprot ID:: Q8WVX9
Molecular weight:: 59356.25

Enzyme Details

3. Fatty acyl-CoA reductase 2

General function:: Involved in catalytic activity
Specific function:: Catalyzes the reduction of fatty acyl-CoA to fatty alcohols. The preferred substrates are C16, C18, C18:1 and C18:2 but low activity can be observed with C10-C14 substrates.
Gene Name:: FAR2
Uniprot ID:: Q96K12
Molecular weight:: 59437.92

Enzyme Details

4. Acyl-CoA wax alcohol acyltransferase 1

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Acyltransferase that predominantly esterify long chain (wax) alcohols with acyl-CoA-derived fatty acids to produce wax esters. Wax esters are enriched in sebum, suggesting that it plays a central role in lipid metabolism in skin. Has a preference for arachidyl alcohol as well as decyl alcohol, demonstrating its relatively poor activity using saturated long chain alcohols (C16, C18, and C20).
Gene Name:: AWAT1
Uniprot ID:: Q58HT5
Molecular weight:: 37758.815

Enzyme Details

5. Acyl-CoA wax alcohol acyltransferase 2

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Acyltransferase that predominantly esterify long chain (wax) alcohols with acyl-CoA-derived fatty acids to produce wax esters. Wax esters are enriched in sebum, suggesting that it plays a central role in lipid metabolism in skin. Has no activity using decyl alcohol and significantly prefers the C16 and C18 alcohols. May also have 2-acylglycerol O-acyltransferase (MGAT) and acyl-CoA:retinol acyltransferase (ARAT) activities, to catalyze the synthesis of diacylglycerols and retinyl esters; however this activity is unclear in vivo.
Gene Name:: AWAT2
Uniprot ID:: Q6E213
Molecular weight:: 38093.25

Transporters

Enzyme Details

1. Platelet glycoprotein 4

General function:: Not Available
Specific function:: Seems to have numerous potential physiological functions. Binds to collagen, thrombospondin, anionic phospholipids and oxidized LDL. May function as a cell adhesion molecule. Directly mediates cytoadherence of Plasmodium falciparum parasitized erythrocytes. Binds long chain fatty acids and may function in the transport and/or as a regulator of fatty acid transport
Gene Name:: CD36
Uniprot ID:: P16671
Molecular weight:: 53054.0

Showing Compound Card for hexadecanol-1 (CDB000267)

Structure for CDB000267 (hexadecanol-1)

Enzymes

Transporters